Tetrahydrofuran → HCID 66815805, compound

HRID 1697107Notes

Reaction equation

HRID 1697107 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[CH3:27])[N:16]=2)[CH:3]=1.[CH2:28]1[CH2:32]O[CH2:30][CH2:29]1>>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](=[O:7])[CH2:30][CH2:29][C:28]2[CH:32]=[CH:4][CH:3]=[CH:2][CH:13]=2)=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[CH3:27])[N:16]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 86624858HCID 86624858, compound

Product 1

HCID 66815805HCID 66815805, compound

Procedure

A solution of 4-chloro-2-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-ylamino]-N-methoxy-N-methyl-benzamide (1.59 g) in THF (20 mL) was cooled in an ice bath, and phenethyl-Grignard solution (10 mL, 1 M in THF) added via syringe. The mixture was stirred overnight at RT, quenched with NH4Cl (aq), extracted with EtOAc, and adsorbed on silica. The product was chromatographed on silica (80 g) (hexane/EtOAc 100:0 to 50:50) (or using DCM/MeOH) to provide 1-{4-chloro-2-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-ylamino]-phenyl}-3-phenyl-propan-1-one.

Workup

  1. customquenched with NH4Cl (aq)
  2. extractionextracted with EtOAc
  3. customThe product was chromatographed on silica (80 g) (hexane/EtOAc 100:0 to 50:50) (or using DCM/MeOH)

Sources & evidence

ORD record
ord-a059063772a14ffe9c721556a95ed712
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

Loading…