Benzamide → HCID 87181084, compound

HRID 390103Notes

Reaction equation

HRID 390103 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][N:15]=3)[N:10]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:9]=2)[CH:5]=[C:4](Cl)[N:3]=1.[C:27]([NH2:35])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:35][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][N:15]=3)[N:10]([S:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)(=[O:18])=[O:19])[CH:9]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 2331BenzamideHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 87180537HCID 87180537, compound

Product 1

HCID 87181084HCID 87181084, compoundYield 32.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of EXAMPLE 14A (290.0 mg, 0.716 mmol), benzamide (95 mg, 0.787 mmol), cesium carbonate (233 mg, 0.716 mmol), palladium (II) acetate (8.03 mg, 0.036 mmol), and Xantphos (31.1 mg, 0.054 mmol) in dioxane (7 mL) and N,N-dimethylformamide (0.6 mL) was heated in a Biotage Initiator microwave reactor at 170° C. for 10 min. The solids were filtered and the filtrate concentrated and purified by flash chromatography eluted with a gradient of 97:5:2.5 to 95:5 dichloromethane/ethyl acetate to give 113 mg (32%) of the title compound.

Workup

  1. filtrationThe solids were filtered
  2. concentrationthe filtrate concentrated
  3. custompurified by flash chromatography
  4. washeluted with a gradient of 97:5:2.5 to 95:5 dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-16aa5cb2ad82479bac692caac1a2cc22
Source dataset
uspto-grants-2013_02
Patent number
US08383624B2

Reaction notes

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