Trimethylphosphine → HCID 67951243, compound

HRID 2401339Notes

Reaction equation

HRID 2401339 reaction equation
[N:1]([CH2:4][C:5]1[O:9][N:8]=[C:7]([CH3:10])[C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=O)=[N+]=[N-].CP(C)C>C1(C)C=CC=CC=1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=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 68983TrimethylphosphineHCID 86666713HCID 86666713, compound

Product 1

HCID 67951243HCID 67951243, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a resealable vial was added crude (2-(5-(azidomethyl)-3-methylisoxazol-4-yl)phenyl) (4-chlorophenyl)methanone (27 mg, 0.077 mmol) and toluene. The vial was sealed and placed under N2 before addition of trimethylphosphine solution (92 μl, 1 M toluene, 0.092 mmol). The reaction was stirred at room temperature for 2 h before purifying via Biotage (10 g, EtOAc/hex) to afford 6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepine. 1H NMR (400 MHz, Acetone) δ 7.78-7.84 (m, 1H), 7.65-7.74 (m, 1H), 7.34-7.47 (m, 6H), 4.62 (br. s, 2H), 2.54 (s, 3H). LC/MS m/z 309 [M+H]+.

Workup

  1. customThe vial was sealed
  2. custombefore purifying via Biotage (10 g, EtOAc/hex)

Sources & evidence

ORD record
ord-5bef2283d359443483da0c87eab36922
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

Loading…