4-Bromo-1-methyl-1H-imidazole → 7-Chloro-2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridine

HRID 1711000Notes

Reaction equation

HRID 1711000 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([Sn](CCCC)(CCCC)CCCC)[S:10][C:3]=12.ClC1C=CN=C2C=C(C3SC=CN=3)SC=12.Br[C:40]1[N:41]=[CH:42][N:43]([CH3:45])[CH:44]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:40]3[N:41]=[CH:42][N:43]([CH3:45])[CH:44]=3)[S:10][C:3]=12

Participants

4

Reactant 3

HCID 12776534-Bromo-1-methyl-1H-imidazoleHCID 221436637-Chloro-2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridineHCID 575166587-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridine

Product 1

HCID 594245247-Chloro-2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridineYield 29%

Procedure

Starting from the compound 98 (scheme 19), following the procedure described above for the synthesis of compound 10 (scheme 2, step 2, example 12) but replacing 2-bromothiazole with 4-bromo-1-methyl-1H-imidazole, title compound 224 was obtained in 29% yield. MS (m/z): 250.1 (100%), 252.1 (37%) (M+1).

Sources & evidence

ORD record
ord-6cc95f6496d443bf9997dd3a95da6329
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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