Triphenylphosphine → HCID 59632228, compound

HRID 2369054Notes

Reaction equation

HRID 2369054 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[C:31]([C:32]2[S:33][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([S:43]([CH3:46])(=[O:45])=[O:44])[CH:38]=3)=[CH:35][CH:36]=2)=[CH:30][C:29]([CH2:47]O)=[N:28]1.C1C(=O)N([Br:56])C(=O)C1>C(Cl)Cl>[Br:56][CH2:47][C:29]1[CH:30]=[C:31]([C:32]2[S:33][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([S:43]([CH3:46])(=[O:45])=[O:44])[CH:38]=3)=[CH:35][CH:36]=2)[N:27]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[Cl:20])[N:28]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 59632050HCID 59632050, compound

Product 1

HCID 59632228HCID 59632228, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PPh3 (4.36 g, 16.62 mmol) was added at 0° C. to a stirred solution of [1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]methanol (6.15 g, 13.85 mmol) in dry DCM. After 30 min, NBS (2.72 g, 15.28 mmol) was added portionwise at 0° C., and the mixture was stirred at it overnight. The solvent was removed in vacuo, and the crude product was purified by flash chromatography (0-50% EtOAc/hexanes) to afford 3-bromomethyl-1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-thiophen-2-yl]-1H-pyrazole as a pale-yellow solid (3.6 g, 54%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product was purified by flash chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fde59e5661494920864754ac2ffaee8f
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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