Ammonia → HCID 66804021, compound

HRID 1843998Notes

Reaction equation

HRID 1843998 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:6]3[CH:20]=[CH:21][NH:22][C:23](=[O:24])[C:5]=3[C:4]=2[CH:3]=1.Br[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[C:32]([F:35])([F:34])[F:33].OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+].N>O.[Cu]I.CS(C)=O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)[C:6]3[CH:20]=[CH:21][N:22]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][C:31]=4[C:32]([F:35])([F:34])[F:33])[C:23](=[O:24])[C:5]=3[C:4]=2[CH:3]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 199372633-Bromo-4-(trifluoromethyl)pyridineHCID 68094318HCID 68094318, compound

Product 1

HCID 66804021HCID 66804021, compoundYield 45.23%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

8-Fluoro-5-(4-methoxybenzyl)-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (I-64b: 0.15 g, 0.00046 mol) was reacted with 3-bromo-4-(trifluoromethyl)pyridine (0.13 g, 0.00058 mol), 8-hydroxy quinoline (0.016 g, 0.00011 mol), K2CO3 (0.19 g, 0.0013 mol), CuI (0.026 g, 0.00013 mol) and DMSO (3 mL) to afford the crude product. The reaction mass was cooled to room temperature, added to ammonia solution in water and extracted with ethyl acetate. The organic layer was washed with brine solution and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 95 mg of the product (45.23% yield).

Workup

  1. customto afford the crude product
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine solution
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customPurification by column chromatography on silica gel (1% methanol in CHCl3)

Sources & evidence

ORD record
ord-4b0b8a7b79fe45da8bd7e2aa29275f1a
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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