Ethanol → 2-benzimidazol-1-yl-N-(2'-chloro-biphenyl-4-yl)-acetamide

HRID 1455617Notes

Reaction equation

[N:1]1([CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)=[O:12])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([O-])([O-])=O.[K+].[K+].[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O.CCO>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[N:1]1([CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[Cl:27])=[CH:16][CH:15]=2)=[O:12])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: 110 °C

Procedure

2-Benzimidazol-1-yl-N-(4-bromophenyl)-acetamide (100 mg, 0.30 mmol) (Example 6A), PdCl2(PPh3)2 (22 mg, 0.03 mmol), K2CO3 (120 mg, 0.8 mmol) and 2-chlorophenylboronic acid (71 mg, 0.45 mmol) were combined and dissolved in DME (0.5 mL), EtOH (0.5 mL) and H2O (0.2 mL). This mixture was heated in a microwave at 110° C. for 10 minutes. SCX purification of the reaction mixture, followed by further purification using prep LCMS yielded the desired product (34 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.21 (2H, s), 7.2-7.3 (2H, m), 7.36-7.45 (5H, m), 7.55 (2H, d, J=8 Hz), 7.67-7.72 (3H, m), 8.25 (1H, s), 10.59 (1H, s). MS (ES) m/z: 362.3 [M+H].

Workup

customSCX purification of the reaction mixture
customfollowed by further purification

Sources & evidence

ORD record: ord-882a1206f2f94dbe97c2d10b8dce9aa9
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482469B2

Reaction notes

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