Potassium Carbonate → HCID 59129329, compound

HRID 1908542Notes

Reaction equation

[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:10]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]3([C:22]([NH:24][C:25]4[CH:26]=[C:27]5[C:31](=[CH:32][CH:33]=4)[NH:30][CH:29]=[C:28]5Br)=[O:23])[CH2:21][CH2:20]3)=[CH:18][C:13]=2[O:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[O:10]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]3([C:22]([NH:24][C:25]4[CH:26]=[C:27]5[C:31](=[CH:32][CH:33]=4)[NH:30][CH:29]=[C:28]5[C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[O:23])[CH2:21][CH2:20]3)=[CH:18][C:13]=2[O:12][CH2:11]1

Participants

Conditions

Temperature: 130 °C

Procedure

Phenyl boronic acid (24.6 mg, 0.204 mmol) was added to a solution of 1-(benzo[d][1,3]-dioxol-5-yl)-N-(3-bromo-1H-indol-5-yl)cyclopropanecarboxamide (39.9 mg, 0.100 mmol) in ethanol (1 mL) containing FibreCat 1001 (6 mg) and 1M aqueous potassium carbonate (0.260 mL). The reaction mixture was then heated at 130° C. in a microwave reactor for 20 minutes. The crude product was then purified by preparative HPLC utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoroacetic acid to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-phenyl-1H-indol-5-yl)cyclopropane carboxamide. ESI-MS m/z calc. 396.2. found 397.3 (M+1)+. Retention time of 3.52 minutes. 1H NMR (400 MHz, DMSO-d6) δ 11.27 (d, J=1.9 Hz, 1H), 8.66 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.65-7.61 (m, 3H), 7.46-7.40 (m, 2H), 7.31 (d, J=8.7 Hz, 1H), 7.25-7.17 (m, 2H), 7.03 (d, J=1.6 Hz, 1H), 6.98-6.87 (m, 2H), 6.02 (s, 2H), 1.43-1.39 (m, 2H), 1.06-1.02 (m, 2H).

Workup

customThe crude product was then purified by preparative HPLC

Sources & evidence

ORD record: ord-95dc6841586e49399f117a5bc1b90982
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598181B2

Reaction notes

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