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

HRID 500852Notes

Reaction equation

HRID 500852 reaction equation
C([Sn](CCCC)CCCC)CCC.[Cl:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]2[CH:21]=[C:22]([C:24]3S[CH:26]=[CH:27][N:28]=3)[S:23][C:16]=12.Br[C:30]1[N:31](C)C=CN=1>>[Cl:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]2[CH:21]=[C:22]([C:24]3[N:31]([CH3:30])[CH:26]=[CH:27][N:28]=3)[S:23][C:16]=12

Participants

4

Reactant 3

HCID 27732622-Bromo-1-methyl-1H-imidazoleHCID 3032732TributylstannanylHCID 221436637-Chloro-2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridine

Product 1

HCID 221435637-chloro-2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridineYield 95%

Procedure

Starting from tributyltin compound 98 (scheme 19) and following the procedure described above for the synthesis of compound 10 (scheme 2, step 2, example 12) but replacing 2-bromothiazole with 2-bromo-1-methyl-1H-imidazole, title compound 214 was obtained in 95% yield. MS (m/z) 250.1 (100%), 252.1 (37%), (M+H).

Sources & evidence

ORD record
ord-1fe60c4c45cd485aa8ab62afd5b64dc2
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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