Acetyl chloride → 7-Acetyl-1-(chloromethyl)-3-(trifluoroacetyl)-1,2-dihydro-3h-benzo[e]indole
Reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]([C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:4]1.[C:22](Cl)([CH3:24])=[O:23]>C1([N+]([O-])=O)C=CC=CC=1>[C:22]([C:14]1[CH:13]=[CH:12][C:10]2[C:11]3[CH:3]([CH2:2][Cl:1])[CH2:4][N:5]([C:16](=[O:21])[C:17]([F:20])([F:18])[F:19])[C:6]=3[CH:7]=[CH:8][C:9]=2[CH:15]=1)(=[O:23])[CH3:24]Participants
Procedure
Acylation of 108 (0.88 g, 2.8 mmol) with AlC3 and AcCl in PhNO2 at 0° C., stirring at room temperature for 16 h, and workup as above, gave a crude product. Chromatography on silica gel, eluting with EtOAc/petroleum ether (from 0:1 to 1:3) gave 7-acetyl-1-(chloromethyl)-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole (110) (196 mg, 33% based on consumption of starting material): mp (EtOAc/petroleum ether) 168-170° C.; 1H NMR (CDCl3) δ 8.52 (d, J=8.9 Hz, 1H), 8.51 (s, 1H), 8.14 (dd, J=8.8, 1.7 Hz, 1H), 8.02 (d, J=9.0 Hz, 1H), 7.84 (d, J=8.8H, 1H), 4.68-4.62 (m, 1H), 4.49-4.41 (m, 1H), 4.28-4.19 (m, 1H), −3.99-3.93 (m, 1H), 3.61-3.55 (m, 1H), 2.74 (s, 3H); 13C NMR δ 197.6, 182.8, 154.9 (q, JC-F 38.4 Hz), 142.1, 134.1, 132.2, 131.3, 131.1, 125.7, 125.5, 131.1, 118.1, 116.0 (q, JC-F 288 Hz), 52.7, 45.4, 42.6, 26.6. Anal. (C17H13ClF3NO2) C, H, N. Further elution gave recovered 108 (360 mg, 40%).
Workup
- customworkup as above, gave a crude product
- washChromatography on silica gel, eluting with EtOAc/petroleum ether (from 0:1 to 1:3)
Sources & evidence
- ORD record
- ord-9dc28eca74f14181ac85fbe20e97dd0c
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07718688B2
Reaction notes
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