1-Phenyl-2,3,4,9-tetrahydro-1H-beta-carboline → HCID 10068843, compound

HRID 1094621Notes

Reaction equation

HRID 1094621 reaction equation
[C:1]1([CH:7]2[C:19]3[NH:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]=3[CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[F:30])[C:24](Cl)=[O:25]>ClCCCl>[F:20][C:21]1[CH:22]=[C:23]([C:24]([N:8]2[CH2:9][CH2:10][C:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[NH:18][C:19]=3[CH:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:25])[CH:27]=[CH:28][C:29]=1[F:30]

Participants

4

Reactant 2

HCID 1989671-Phenyl-2,3,4,9-tetrahydro-1H-beta-carbolineHCID 27245193,4-Difluorobenzoyl chloride

Product 1

HCID 10068843HCID 10068843, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
55 °C

Procedure

The title compound was prepared by the addition of 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline (95 mg, 383 μmol), DCE (5 mL), 3,4-difluorobenzoyl chloride (88 mg, 498 μmol), and TEA (1.0 mL) to a 25 mL flask. The solution was allowed to stir at 55° C. for 16 hours. The reaction solution was concentrated, and the crude sample was chromatographed (SiO2, 100% hexane to 25% EtOAc) to yield 53 mg of title compound; 1H NMR (CDCl3) δ 8.02 (1H, br s), 7.53 (1H, d), 7.30-7.33 (6H, m), 7.15-7.23 (5H, m), 7.07 (1H, br s), 3.75 (1H, m), 3.41 (1H, m), 2.93 (1H, m), 2.84 (1H, dd); MS (ESI): 389 (MH+).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe crude sample was chromatographed (SiO2, 100% hexane to 25% EtOAc)

Sources & evidence

ORD record
ord-c1bcd1dab38841c7bdc5c3cadf9596d3
Source dataset
uspto-grants-2012_03
Patent number
US08133992B2

Reaction notes

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