Acetone → 2-(2-nitrophenyl)-Thiazolo[5,4-b]pyridine-6-methanol

HRID 1799093Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([C:19](OC)=[O:20])=[CH:14][N:13]=2)([O-:3])=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].CC(C)=O.[O-]S([O-])=O.[Na+].[Na+]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([CH2:19][OH:20])=[CH:14][N:13]=2)([O-:3])=[O:2]

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of methyl 2-(2-nitrophenyl)thiazolo[5,4-b]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 −60° C. 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-b]pyridin-6-yl)methanol (50% yield).

Workup

customThe resultant solids were removed by filtration
washrinsed with THF
concentrationThe combined organics were concentrated in vacuo
customthe crude residue crystallized from CH2Cl2

Sources & evidence

ORD record: ord-648cd71498164daca865e58763ac91a7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343997B2

Reaction notes

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