6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole → HCID 178454010, compound

HRID 2271690Notes

Reaction equation

HRID 2271690 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:27])[O-:26])[CH2:20][CH2:19]1.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[CH:38][C:39]3[N:43]=[CH:42][NH:41][C:40]=3[CH:44]=2)O1>>[NH:41]1[C:40]2[CH:44]=[CH:36][C:37]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]=[CH:7][C:6]([C:12]([CH:14]3[CH2:15][CH2:16]3)=[O:13])=[C:5]4[NH:17][C@H:18]3[CH2:19][CH2:20][C@H:21]([NH:24][C:25](=[O:27])[O:26][C:4]([CH3:9])([CH3:5])[CH3:3])[CH2:22][CH2:23]3)=[CH:38][C:39]=2[N:43]=[CH:42]1

Participants

3

Reactant 2

HCID 467380066-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazoleHCID 178526093HCID 178526093, compound

Product 1

HCID 178454010HCID 178454010, compoundYield 172.4%

Procedure

Following general procedure D, tert-butyl [trans-4-(6-bromo-3-(cyclopropanecarbonyl)quinolin-4-ylamino]cyclohexylcarbamate (49 mg, 0.100 mmol) was reacted with 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole (49 mg, 0.200 mmol) to afford the desired product (45.3 mg, 86%) as an off-white solid: ESI MS m/z 526 [C31H35N5O3+H]+.

Sources & evidence

ORD record
ord-fd7b653f5e2340fea1c628af767d3e67
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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