2-Bromothiazole → 7-Chloro-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)thieno[3,2-b]pyridine

HRID 500798Notes

Reaction equation

HRID 500798 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]([CH2:51][O:52][CH2:53][CH2:54][Si:55]([CH3:58])([CH3:57])[CH3:56])[CH:48]=[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]([CH2:51][O:52][CH2:53][CH2:54][Si:55]([CH3:58])([CH3:57])[CH3:56])[CH:48]=[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 575166587-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridineHCID 594245422-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole

Product 1

HCID 594246707-Chloro-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)thieno[3,2-b]pyridine

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 108, title compound 109 was obtained as a white solid (22 mg, 41% yield). MS (m/z) 366.1/368.1 (M+H).

Sources & evidence

ORD record
ord-dd8ce9baf0b24df18b1b13725a4bef29
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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