(2-(2-Bromoethoxy)ethoxy)(tert-butyl)diphenylsilane → 3-Benzyl 1-methyl 4-(1-(2-(2-(tert-butyldiphenylsilyloxy)ethoxy)ethyl)-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalate

HRID 529019Notes

Reaction equation

HRID 529019 reaction equation
[CH2:1]([N:5]([CH2:33][CH2:34][CH2:35][CH3:36])[C:6]([C:8]1[N:9]=[C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[NH:11][CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].Br[CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][Si:44]([C:57]([CH3:60])([CH3:59])[CH3:58])([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[Si:44]([O:43][CH2:42][CH2:41][O:40][CH2:39][CH2:38][N:11]1[CH:12]=[C:8]([C:6](=[O:7])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:33][CH2:34][CH2:35][CH3:36])[N:9]=[C:10]1[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])([C:57]([CH3:59])([CH3:60])[CH3:58])([C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

3

Reactant 2

HCID 86718937(2-(2-Bromoethoxy)ethoxy)(tert-butyl)diphenylsilaneHCID 178449065HCID 178449065, compound

Product 1

HCID 710623583-Benzyl 1-methyl 4-(1-(2-(2-(tert-butyldiphenylsilyloxy)ethoxy)ethyl)-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalateYield 85.6%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 274A, 3-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalate (200 mg, 0.40 mmol) and (2-(2-bromoethoxy)ethoxy)(tert-butyl)diphenylsilane (165 mg, 0.40 mmol) were converted to the title compound (280 mg, 84%). 1H NMR (CDCl3) δ 8.66 (d, J=2.0 Hz, 1H), 8.16 (dd, J=8.0, 2.0 Hz, 1H), 7.62-7.57 (m, 4H), 7.57 (s, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.42-7.32 (m, 9H), 7.24-7.22 (m, 2H), 5.12 (s, 2H), 3.96 (s, 3H), 3.94-3.85 (m, 2H), 3.69-3.63 (m, 4H), 3.46-3.43 (m, 4H), 3.67 (t, J=5.2 Hz, 2H), 1.65-1.55 (m, 4H), 1.40-1.15 (m, 4H), 1.01 (s, 9H), 1.00-0.85 (m, 6H); MS(ESI+) m/z 819.4 (M+H)+.

Sources & evidence

ORD record
ord-e32bc6cb727d45969d250862fd64b5b0
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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