Triphenylphosphine → HCID 59632195, compound

HRID 2369056Notes

Reaction equation

HRID 2369056 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N:20]([C:23]([C:26]1[CH:30]=[C:29]([C:31]2[S:32][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([S:42]([CH3:45])(=[O:44])=[O:43])[CH:37]=3)=[CH:34][CH:35]=2)[N:28]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[Cl:52])[N:27]=1)([CH3:25])[CH3:24])=[N+]=[N-]>C1COCC1.O>[Cl:52][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=1[N:28]1[C:29]([C:31]2[S:32][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([S:42]([CH3:45])(=[O:43])=[O:44])[CH:37]=3)=[CH:34][CH:35]=2)=[CH:30][C:26]([C:23]([NH2:20])([CH3:24])[CH3:25])=[N:27]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 59632456HCID 59632456, compound

Product 1

HCID 59632195HCID 59632195, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

PPh3 (3.3 g, 12.58 mmol) was added at rt to a solution of the 3-(2-azidopropan-2-yl)-1-(2-chlorophenyl)-5-(5-(3-(methylsulfonyl)phenyl)thiophen-2-yl)-1H-pyrazole) (3.08 g, 6.185 mmol) in a mixture of THF—H2O (6:1, 70 mL), and the resulting mixture was stirred at it under N2 for 8d. The solvent was removed in vacuo, and the residue was partitioned between water and EtOAc. The two phases were separated, and the aqueous phase was extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-60% 20% MeOH/DCM) to give the title compound as a light-yellow solid (2.43 g, 89%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.83-7.80 (m, 1H), 7.73-7.71 (m, 1H), 7.56-7.41 (m, 5H), 7.19 9d, 1H), 6.72 9d, 1H), 6.63 (s, 1H), 3.07 (s, 3H), 2.43 (brs, 2H), 1.61 (s, 6H). MS(ES) 455 (M-NH2).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water and EtOAc
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo
  8. customThe crude product was purified by flash chromatography (0-60% 20% MeOH/DCM)

Sources & evidence

ORD record
ord-0e0a9afe162c4b2796f44eea8ff19b6c
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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