Yield:1231952-71-8 50%

Reaction Conditions:

Stage #1: methyl 2-(2-nitrophenyl)thiazolo[5,4-b]pyridine-6-carboxylatewith lithium aluminium tetrahydride in tetrahydrofuran at -60 - -55; for 12 h;
Stage #2: with water;acetone;sodium sulfite in tetrahydrofuran;

Steps:

1

A solution of methyl 2-(2-nitrophenyl)thiazolo[5,4-δ]pyridine-6-carboxylate (1 eq) in THF was added over 8 h to a mixture of lithium aluminum hydride (LAH) (4.4 eq) in THF maintaining the internal temperature at -55°C. The reaction mixture was stirred an additional 4 h at -60⁰C. Acetone (18 eq) was added followed by sat. aq Na₂SO₃. The resultant solids were removed by filtration and rinsed with THF. The combined organics were concentrated in vacuo and the crude residue crystallized from CH₂Cl₂ to give (2-(2-nitrophenyl)thiazolo[5,4-δ]pyridin-6-yl)methanol (50 % yield)

References:

WO2010/71853,2010,A1 Location in patent:Page/Page column 68; 69