2-Bromothiazole → Methyl 2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazole-5-carboxylate

HRID 500802Notes

Reaction equation

HRID 500802 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.BrC1SC=CN=1.Br[C:46]1[N:47]([CH3:55])[C:48]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][N:50]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:46]3[N:47]([CH3:55])[C:48]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][N:50]=3)[S:10][C:3]=12

Participants

5

Reactant 4

HCID 764302-BromothiazoleHCID 221436637-Chloro-2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridineHCID 26343677Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylateHCID 575166587-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridine

Product 1

HCID 59424560Methyl 2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazole-5-carboxylate

Procedure

Starting from the compound 98 (scheme 19) and following the procedure described above for the synthesis of compound 10 (example 12, scheme 2) but substituting 2-bromothiazole in the step 2 for the bromide 118, title compound 119 was obtained as a white solid (580 mg, 100% yield). MS (m/z) 308.1/310.0 (M+H).

Sources & evidence

ORD record
ord-ae251a2e753c46758971fab19a4aac10
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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