Cesium carbonate → HCID 58677674, compound

HRID 1012604Notes

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]=[CH:23][C:22]([C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[O:26])=[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]=[CH:23][C:22]([C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:26])=[CH:21][C:20]=1[CH3:33])=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Bromo-5-fluorotoluene (56 μL, 0.44 mmol) was dissolved in 3 mL dry 1,4-dioxane in a vial under an argon atmosphere. Compound 468 (132 mg, 0.37 mmol) was added and dissolved in the solvent. Rac-BINAP (8.6 mg, 0.014 mmol), Pd2(dba)3 (8.5 mg, 0.009 mmol) and Cs2CO3 (169 mg, 0.52 mmol) were added, and the reaction mixture was stirred under an argon atmosphere at 100° C. for 48 h. The reaction mixture was filtered and then purified by flash chromatography using EtOAc/DCM 1:3 as the eluent to afford the title compound as yellow foam. 13C NMR (CDCl3) δ 195.5, 169.8, 160.7, 150.2, 141.1, 138.1, 137.2, 136.5, 135.7, 134.2, 133.6, 129.7, 129.2, 127.3, 127.3, 123.9, 117.9, 115.2, 113.9, 111.5, 66.9, 48.2, 42.5, 20.2, 18.1

Workup

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

Sources & evidence

ORD record: ord-fee20129bf44405ca8c22a7f2d710c9c
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977387B2

Reaction notes

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