Cyclopropylboronic acid → HCID 25160970, compound

HRID 914031Notes

Reaction equation

HRID 914031 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][O:11][CH2:12][C:13]3([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)[N:7]([CH2:26][CH:27]3[CH2:29][CH2:28]3)[C:6]=2[CH:30]=1.[CH:31]1(B(O)O)[CH2:33][CH2:32]1.C(C1C=CC(C2C=CC3N(CC4CC4)C(COCC4(C5C=CC=CC=5)CCN(C(OC(C)(C)C)=O)CC4)=NC=3C=2)=CC=1)#N>>[CH:31]1([C:2]2[CH:3]=[CH:4][C:5]3[N:9]=[C:8]([CH2:10][O:11][CH2:12][C:13]4([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]4)[N:7]([CH2:26][CH:27]4[CH2:29][CH2:28]4)[C:6]=3[CH:30]=2)[CH2:33][CH2:32]1

Participants

4

Reactant 3

HCID 2760897Cyclopropylboronic acidHCID 25160966HCID 25160966, compoundHCID 67403049HCID 67403049, compound

Product 1

HCID 25160970HCID 25160970, compoundYield 92%

Procedure

Suzuki coupling reaction of 6-Bromo-1-(cyclopropylmethyl)-2-(((1-methyl-4-phenylpiperidin-4-yl)methoxy)methyl)-1H-benzo[d]imidazole (12 mg, 0.026 mmol) with cyclopropylboronic acid (3 equiv.) following the procedure described for the synthesis of tert-butyl 4-(((5-(4-cyanophenyl)-1-(cyclopropylmethyl)-1H-benzo[d]imidazol-2-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate, gave 13 mg of the title compound (92% yield). LC/MS (HPLC method 8): tR=0.8 min, 430(MH)+.

Sources & evidence

ORD record
ord-56fb500ee57d47ac9a99e27e838ace19
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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