Ethyl 2-(methylsulfanyl)-1,3-benzothiazole-6-carboxylate → (2-(Methylthio)thiazolo[4,5-b]pyridin-6-yl)methanol

HRID 1848104Notes

Reaction equation

HRID 1848104 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[C:6]([N:16]=1)=[N:7][CH:8]=[C:9]([C:11](OCC)=[O:12])[CH:10]=2.CSC1SC2C=C(C(OCC)=O)C=CC=2N=1>>[CH3:1][S:2][C:3]1[S:4][C:5]2[C:6]([N:16]=1)=[N:7][CH:8]=[C:9]([CH2:11][OH:12])[CH:10]=2

Participants

3

Reactant 2

HCID 86680993Ethyl 2-(methylsulfanyl)-1,3-benzothiazole-6-carboxylateHCID 86681077Ethyl 2-(methylthio)thiazolo[4,5-b]pyridine-6-carboxylate

Product 1

HCID 86681080(2-(Methylthio)thiazolo[4,5-b]pyridin-6-yl)methanol

Procedure

(2-(Methylthio)thiazolo[4,5-b]pyridin-6-yl)methanol was synthesized as a white solid (404 mg, 67%) using a procedure analogous to that described in Step 3 of Example 36, substituting ethyl 2-(methylthio)thiazolo[4,5-b]pyridine-6-carboxylate from the previous step for ethyl 2-(methylthio)benzo[d]thiazole-6-carboxylate used in Example 36. 1H NMR (300 MHz, DMSO-d6) δ 8.51 (d, J=1.9 Hz, 1H), 8.42 (d, J=1.9 Hz, 1H), 5.44 (t, J=5.7 Hz, 1H), 4.63 (d, J=5.7 Hz, 2H), 2.82 (s, 3H); LCMS (ESI) m/z 213 (M+H)+.

Sources & evidence

ORD record
ord-e6c83d85fdf64ff39e6103e8391a2c73
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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