Sodium Carbonate → HCID 68181124, compound

HRID 2371284Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:20](=[O:37])[N:21]([C:28]2[O:36][C:32]3=[CH:33][CH:34]=[CH:35][C:31]3=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.[C:39]1(B(O)O)[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.CCO.O.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:1][O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:20](=[O:37])[N:21]([C:28]2[O:36][C:32]3=[CH:33][CH:34]=[CH:35][C:31]3=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]=3)=[CH:15][CH:14]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A solution consisting of 4-[2-(4-Benzofuran-2-ylphenylcarbamoyl)-3-(4-bromo phenyl)-propyl]-benzoic acid methyl ester (200 mg, 0.35 mmol), dichlorobis(tri-o-tolyl phosphine)-palladium(II), 1-cyclohexenyl boronic acid (222 mg, 1.76 mmol) and sodium carbonate (373 mg, 3.5 mmol) in DME (8 mL), EtOH (4 mL) and water (2 mL) was heated at 125° C. for 7 min in the microwave. The crude reaction mixture was partitioned between EtOAc and water. Evaporation of the organic portion afforded crude 4-[2-(4-Benzofuran-2-ylphenylcarbamoyl)-3-(4-cyclohex-1-enylphenyl)-propyl]-benzoic acid methyl ester which was carried on as is for the next step. LC-MS m/z=570 [C38H35NO4+H]+.

Workup

customThe crude reaction mixture
customwas partitioned between EtOAc and water
customEvaporation of the organic portion

Sources & evidence

ORD record: ord-1d2284e521b245e3a26826b4480fb02e
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710236B2

Reaction notes

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