ChemicalBook CAS DataBase List 4-HYDROXYMETHYL-7-AZAINDOLE

4-HYDROXYMETHYL-7-AZAINDOLE synthesis

7synthesis methods

Product Name:4-HYDROXYMETHYL-7-AZAINDOLE
CAS Number:936549-95-0
Molecular formula:C8H8N2O
Molecular Weight:148.16

ethyl 1H-pyrrolo[2,3-b]pyridine-4-carboxylate

1261588-72-0
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$87.90/250mg

936549-95-0
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$45.00/10mg

Yield: 67%

Reaction Conditions:

with sodium tetrahydroborate;calcium chloride in tetrahydrofuran for 6 h;Reflux;

Steps:

II
To the solution of Int-8 (9.5 g, 50 mmol) in THF (150 mL) was added sodium borohydride (3.8 g, 100 mmol) and calcium chloride (11.Ig, 100 mmol), and the mixture was heated to reflux for 6 h. After the reaction was complete (by TLC), methanol and water were added, the resulting mixture was extracted with ethyl acetate. The organic layer was washed by water, brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford Int-9 (5.0 g, 67%).1H NMR (400 MHz, DMSO-^₆) δ 11.84 (brs, IH), 8.22 (d, J= 5.6 Hz, IH), 7.51 (t, J = 2.8 Hz, IH), 7.31 (d, J= 6.4 Hz, IH), 6.74 (q, J= 1.6 Hz, IH), 5.65 (t, J= 6.0 Hz, IH), 4.92 (d, J= 5.2 Hz, 2H).

References:

ASCEPION PHARMACEUTICALS, INC.;JIANG, Shan;XING, Xinglong;WANG, Qishan;KONG, Ren WO2011/23081, 2011, A1 Location in patent:Page/Page column 53

728034-12-6 Synthesis