1-Chloro-4-iodobenzene → HCID 69411490, compound

HRID 857487Notes

Reaction equation

HRID 857487 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH:13]=[CH2:14])=[C:11]2[CH2:15][N:16]([CH:19]([CH3:21])[CH3:20])[C:17](=[O:18])[C:10]2=[N:9]1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][CH:24]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH:13]=[CH:14][C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)=[C:11]2[CH2:15][N:16]([CH:19]([CH3:21])[CH3:20])[C:17](=[O:18])[C:10]2=[N:9]1

Participants

4

Reactant 2

HCID 125101-Chloro-4-iodobenzeneHCID 11347161HCID 11347161, compound

Product 1

HCID 69411490HCID 69411490, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

To a stirred solution of 2-(2-chloro-phenyl)-5-isopropyl-3-vinyl-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one 1A-8 (42 mg), palladium acetate (3 mg) and 4-chloroiodobenzene (300 mg) were stirred for 18 hours. The reaction was concentrated and chromatographed on silica gel (gradient 30% to 60% ethyl acetate/hexanes) to afford the title compound (1A-39), 44 mg. 1H NMR in d6-DMSO (ppm): δ 7.78 (d, 1H), 7.63–7.38 (m, 5H), 7.13 (d, 1H), 6.61 (d, 1H), 4.62 (s, 2H), 4.40 (m, 1H), 1.23 (d, 6H); ms (LCMS) m/z=412.3 (M+1)+.

Workup

  1. concentrationThe reaction was concentrated
  2. customchromatographed on silica gel (gradient 30% to 60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4c61cad8c9e5403d8d0413d914dc76fc
Source dataset
uspto-grants-2006_12
Patent number
US07145012B2

Reaction notes

Loading…