Imidazo(4,3-b)(1,3)thiazole-7-carbaldehyde → 7-[(5-Methylthiopyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazole

HRID 1072335Notes

Reaction equation

HRID 1072335 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([S:8][CH3:9])[CH:7]=1.C([Li])CCC.CCCCCC.[CH:21]([C:23]1[N:24]=[CH:25][N:26]2[CH:30]=[CH:29][S:28][C:27]=12)=[O:22]>>[CH3:9][S:8][C:6]1[CH:7]=[C:2]([CH:21]([OH:22])[C:23]2[N:24]=[CH:25][N:26]3[CH:30]=[CH:29][S:28][C:27]=23)[CH:3]=[N:4][CH:5]=1

Participants

4

Reactant 3

HCID 22390357Imidazo(4,3-b)(1,3)thiazole-7-carbaldehydeHCID 223903593-Bromo-5-(methylthio)pyridineHCID 178418244HCID 178418244, compound

Product 1

HCID 223903167-[(5-Methylthiopyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazoleYield 64%

Procedure

7-[(5-Methylthiopyridin-3-yl)hydroxymethyl]imidazo-[5,1-b]thiazole (119 mg) was prepared in substantially the same manner as in step a) of Synthesis Example 5, except that 204 mg of 3-bromo-5-methylthiopyridine, 0.656 ml of a 1.6 N n-butyllithium/n-hexane solution, and 102 mg of 7-formylimidazo[5,1-b]thiazole were used as the starting materials.

Workup

  1. customof Synthesis Example 5

Sources & evidence

ORD record
ord-c30938443d744290a16789e492312dee
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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