2-Bromo-N,N-dibutyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamide → 3-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)isophthalate

HRID 529008Notes

Reaction equation

HRID 529008 reaction equation
CC1(C)COB([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])OC1.Br[C:30]1[N:31]([CH2:46][O:47][CH2:48][CH2:49][Si:50]([CH3:53])([CH3:52])[CH3:51])[CH:32]=[C:33]([C:35]([N:37]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH2:40][CH3:41])=[O:36])[N:34]=1>>[CH2:38]([N:37]([CH2:42][CH2:43][CH2:44][CH3:45])[C:35]([C:33]1[N:34]=[C:30]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=2[C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[N:31]([CH2:46][O:47][CH2:48][CH2:49][Si:50]([CH3:52])([CH3:51])[CH3:53])[CH:32]=1)=[O:36])[CH2:39][CH2:40][CH3:41]

Participants

3

Reactant 2

HCID 710622212-Bromo-N,N-dibutyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamideHCID 710623233-Benzyl 1-methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)isophthalate

Product 1

HCID 710623853-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)isophthalateYield 62.7%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 264I, 3-benzyl 1-methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)isophthalate (1.76 g, 4.62 mmol) and 2-bromo-N,N-dibutyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamide (1.0 g, 2.31 mmol) were converted to the title compound (900 mg, 62%). 1H NMR (CDCl3) δ 8.66 (d, J=1.6 Hz, 1H), 8.23 (dd, J=8.0, 1.6 Hz, 1H), 7.62 (s, 1H), 7.58 (d, J=7.6 Hz, 1H), 7.36-7.32 (m, 3H), 7.25-7.23 (m, 2H), 5.14 (s, 2H), 4.87 (s, 2H), 3.97 (s, 3H), 3.89 (br s, 2H), 3.45 (br s, 2H), 3.34 (t, J=8.0 Hz, 2H), 1.60-1.54 (m, 2H), 1.39-1.21 (m, 6H), 0.95-0.78 (m, 6H), 0.76 (t, J=8.0 Hz, 2H), −0.06 (s, 9H); MS(ESI+) m/z 622.2 (M+H)+.

Sources & evidence

ORD record
ord-5debdddde1054ac5a480dec38875330b
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

Loading…