Trimethylphosphine → 4H-Isoxazolo[3,4-d][2]benzazepine, 6-(4-chlorophenyl)-1,4-dimethyl-

HRID 2401356Notes

Reaction equation

HRID 2401356 reaction equation
[N:1]([CH:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=O)=[C:9]([CH3:26])[O:8][N:7]=1)[CH3:5])=[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:10]3=[C:9]([CH3:26])[O:8][N:7]=[C:6]3[CH:4]([CH3:5])[N:1]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 68983TrimethylphosphineHCID 86666719HCID 86666719, compound

Product 1

HCID 573888494H-Isoxazolo[3,4-d][2]benzazepine, 6-(4-chlorophenyl)-1,4-dimethyl-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a round bottomed flask was added (2-(3-(1-azidoethyl)-5-methylisoxazol-4-yl)phenyl)(4-chlorophenyl)methanone (0.073 g, 0.199 mmol), toluene, and trimethylphosphine (0.239 mL, 1M in toluene, 0.239 mmol). The reaction was stirred at room temperature overnight before concentrating. The crude residue was purified via Biotage (EtOAc/hex) to afford impure 6-(4-chlorophenyl)-1,4-dimethyl-4H-benzo[c]isoxazolo[4,3-e]azepine. This material was purified via preparatory HPLC and the fractions neutralized before being extracted with EtOAc. The organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford 6-(4-chlorophenyl)-1,4-dimethyl-4H-benzo[c]isoxazolo[4,3-e]azepine (0.0011 g, 0.003 mmol). 1H NMR (400 MHz, Acetone-d6) δ 7.74-7.70 (m, 1H), 7.69-7.63 (m, 1H), 7.49-7.41 (m, 3H), 7.41-7.33 (m, 3H), 4.24-4.16 (m, 1H), 2.66 (s, 3H), 1.86 (d, J=6.35 Hz, 3H); LC/MS m/z 323 [M+H]+.

Workup

  1. concentrationbefore concentrating
  2. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-b071e6c313b3468c90a84e3f208c7cb2
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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