Acetamide → HCID 69135179, compound

HRID 969531Notes

Reaction equation

HRID 969531 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH3:19])[C:13]=2[CH:12]=[C:11](Br)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([NH2:24])(=[O:23])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+].ClCCl>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].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>[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH3:19])[C:13]=2[CH:12]=[C:11]([NH:24][C:21](=[O:23])[CH3:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 178AcetamideHCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 69134260HCID 69134260, compound

Product 1

HCID 69135179HCID 69135179, compoundYield 62.1%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 10 g (30.2 mmol) 4-benzyloxy-6-bromo-1,2-dimethyl-1H-benzimidazole, 2.1 g (36.2 mmol) acetamide, 524 mg (0.9 mmol) xantphos, 13.7 g (42.3 mmol) cesium carbonate and 276 mg (0.3 mmol) Pd2(dba)3 in 60 ml dioxane was stirred at 100° C. for 20 h. The reaction mixture was cooled to room temperature and poured into dichloromethane. The precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (toluene/dioxane=2:1) to afford 5.8 g (62%) of the title compound as a white foam.

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (toluene/dioxane=2:1)

Sources & evidence

ORD record
ord-be484a5df0324bdd9deab66dab2ad6d8
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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