Cyclopropylboronic acid → Benzyl 2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 1409464Notes

Reaction equation

HRID 1409464 reaction equation
Br[C:2]1[N:3]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:4]=[C:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:6]=1.[CH:25]1(B(O)O)[CH2:27][CH2:26]1>>[CH:25]1([C:2]2[N:3]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:4]=[C:5]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])[N:6]=2)[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 2760897Cyclopropylboronic acidHCID 70980971Benzyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Product 1

HCID 70981388Benzyl 2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Procedure

The title compound was prepared using the procedure described in Example 59(a) starting from benzyl 2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (7.31 mmol, 3 g) and cyclopropylboronic acid (14.63 mmol, 1.25 g). Yield 1.02 g. 1H-NMR (400 MHz; CDCl3): δ −0.02 (s, 9H), 0.91 (t, 2H), 0.99 (bs, 2H), 1.15 (bs, 2H), 1.87-1.94 (m, 1H), 3.52 (t, 2H), 5.32 (s, 2H), 5.34 (s, 2H), 7.29-7.43 (m, 5H), 7.59 (s, 1H). LC-MS: [M+1]=373.31.

Sources & evidence

ORD record
ord-d89dd436bc4b4106a3a91ec5d7d8b440
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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