Triphenylarsine → HCID 69158755, compound

HRID 1392709Notes

Reaction equation

C[Sn](C)(C)[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:11][CH:10]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1.[CH:19]1([NH:22][C:23]([C:25]2[C:34](=[O:35])[C:33]3[C:28](=[N:29][CH:30]=[CH:31][CH:32]=3)[N:27]([C:36]3[CH:41]=[C:40](Br)[CH:39]=[C:38]([Br:43])[CH:37]=3)[CH:26]=2)=[O:24])[CH2:21][CH2:20]1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.CCOC(C)=O.O.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]>[Br:43][C:38]1[CH:39]=[C:40]([C:3]2[CH:8]=[CH:7][C:6]([CH:9]3[CH2:11][CH:10]3[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=2)[CH:41]=[C:36]([N:27]2[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][N:29]=3)[C:34](=[O:35])[C:25]([C:23]([NH:22][CH:19]3[CH2:20][CH2:21]3)=[O:24])=[CH:26]2)[CH:37]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of ester from step 2 (1.7 eq), dibromo from step 1 (1 eq), Pd2(dba)3 (0.05 eq) and triphenylarsine (0.25 eq) in DMF (0.05M) was heated at 80° C. for 2 h. The mixture was cooled to rt, diluted with EtOAc and water, the organic was washed with brine, dried and solvent evaporated. The residue was purified by flash chromatography (CH2Cl2:MeOH; 99:1 to 90:10) to afford the title compound.

Workup

temperatureThe mixture was cooled to rt
washthe organic was washed with brine
customdried
customsolvent evaporated
customThe residue was purified by flash chromatography (CH2Cl2:MeOH; 99:1 to 90:10)

Sources & evidence

ORD record: ord-d78fb4e02f3049d99d485f84b1b6469f
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342024B2

Reaction notes

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