Potassium Carbonate → HCID 86723164, compound

HRID 868876Notes

Reaction equation

HRID 868876 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[N+:17]([O-:19])=[O:18].Br[CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24]>C(#N)C>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24])[CH:12]=[C:11]2[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27251143-Bromo-1,1,1-trifluoropropaneHCID 263381955-Chloro-3-nitro-1H-indole

Product 1

HCID 86723164HCID 86723164, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (1.5 g, 11.1 mmol) was added to a solution of 5-chloro-3-nitro-indole (1.1 g, 5.6 mmol) and 3-bromo-1,1,1-trifluoropropane (1.2 g, 6.7 mmol) in ACN (20 mL) at rt. The mixture was heated to 80° C. and stirred overnight. The reaction mixture was filtered and concentrated to give 1.6 g (100%) of the title compound as a brown solid. 1H NMR (400 MHz, CDCl3): δ 2.69-2.76 (2H, m), 4.47 (2H, t, J=7.2 Hz), 7.31 (1H, d, J=8.8 Hz), 7.38 (1H, dd, J=2.0, 8.8 Hz), 8.11 (1H, s), 8.30 (1H, d, J=2.0 Hz).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-af95f122649f4d859bb8df645e1a9a5d
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

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