Potassium Carbonate → HCID 90031330, compound

HRID 56193Notes

Reaction equation

HRID 56193 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11].C([O-])([O-])=O.[K+].[K+].[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1[CH2:27][CH2:28][NH2:29]>C(Cl)Cl>[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1[CH2:27][CH2:28][NH:29][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 4397522-(1H-indol-2-yl)ethanamine

Product 1

HCID 90031330HCID 90031330, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1,2-difluoro-4-nitrobenzene (1.59 g, 10 mmol) and K2CO3 (6.90 g, 50 mmol) in DCM (40 mL) was added 2-(1H-indol-2-yl)ethanamine (1.96 g, 10 mmol) in one portion under N2 and the mixture was stirred at rt for 24 h. The mixture was then filtered, and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1) to give the title compound as a yellow solid (2.32 g, 78%).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1)

Sources & evidence

ORD record
ord-0a3520af49d84172bbb6643a1d6cd199
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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