Cesium carbonate → HCID 11282738, compound

HRID 1012597Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[CH:24]=[C:23]([C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[O:26])[CH:22]=[CH:21][C:20]=2[CH3:33])=[O:18])=[C:13]([Cl:34])[CH:12]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:34][C:13]1[CH:12]=[C:11]([NH:10][C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=2[CH3:9])[CH:16]=[CH:15][C:14]=1[C:17]([C:19]1[CH:24]=[C:23]([C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:26])[CH:22]=[CH:21][C:20]=1[CH3:33])=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Bromo-5-fluorotoluene (47 μL, 0.37 mmol) was dissolved in 3 mL dry 1,4-dioxane in a vial under an argon atmosphere. Compound 404 (110 mg, 0.31 mmol) was added and dissolved in the solvent. Rac-BINAP (7.3 mg, 0.012 mmol), Pd2(dba)3 (7.0 mg, 0.008 mmol) and Cs2CO3 (141 mg, 0.43 mmol) were added, and the reaction mixture was stirred under an argon atmosphere at 100° C. for 72 h. The reaction mixture was filtered and then purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) (v:v=0:100 to 50:50) as the eluent to afford the title compound as brown oil. 13C NMR (CDCl3) δ 195.4, 169.7, 160.6, 150.3, 139.8, 139.7, 136.6, 135.4, 134.0, 133.7, 132.4, 131.5, 129.2, 127.9, 127.4, 127.0, 117.8, 115.0, 113.8, 111.7, 66.8, 48.3, 42.8, 20.2, 18.1.

Workup

dissolutiondissolved in the solvent
filtrationThe reaction mixture was filtered
custompurified by continuous gradient flash chromatography

Sources & evidence

ORD record: ord-322a210984154680aa1dde8a4a246dd4
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977387B2

Reaction notes

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