Triphenylphosphine → HCID 57405437, compound

HRID 1772384Notes

Reaction equation

HRID 1772384 reaction equation
[N:1]([CH2:4][C:5]1[O:9][N:8]=[C:7]([CH3:10])[C:6]=1[C:11]1[C:12]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=O)=[N:13][N:14]([CH3:16])[CH:15]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[C:12]3[C:11](=[CH:15][N:14]([CH3:16])[N:13]=3)[C:6]3[C:7]([CH3:10])=[N:8][O:9][C:5]=3[CH2:4][N:1]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86666732HCID 86666732, compound

Product 1

HCID 57405437HCID 57405437, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-(5-(azidomethyl)-3-methylisoxazol-4-yl)-1-methyl-1H-pyrazol-3-yl)(4-chlorophenyl)methanone (0.03 g, 0.08 mmol) in anhydrous THF (10 mL), was added triphenylphosphine (32 mg, 0.12 mmol) at room temperature. The mixture was stirred for 12 h at room temperature. The mixture was concentrated and the residue was purified by flash chromatography eluting with (petroleum ether/ethyl acetate=1:3) to afford the title compound as a white solid (15 mg, 60% yield). LC/MS: m/z 312 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 7.62 (d, J=9 Hz, 3H), 7.36 (d, J=9 Hz, 2H), 4.87 (s, 2H), 4.08 (s, 3H), 2.45 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash chromatography
  3. washeluting with (petroleum ether/ethyl acetate=1:3)

Sources & evidence

ORD record
ord-4c9466af2f7e4494a9547f1a41dd96eb
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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