Water → HCID 6538749, compound

HRID 397306Notes

Reaction equation

HRID 397306 reaction equation
[CH2:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12](=[O:14])[CH2:11][C:10]3[C:15]4[C:20]([NH:21][C:9]=3[C:8]=2[CH:26]=1)=[CH:19][CH:18]=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:16]=4)[CH:2]=[CH2:3].[OH2:27]>CN(C=O)C.Cl[Pd]Cl>[O:27]=[C:2]([CH3:3])[CH2:1][C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12](=[O:14])[CH2:11][C:10]3[C:15]4[C:20]([NH:21][C:9]=3[C:8]=2[CH:26]=1)=[CH:19][CH:18]=[C:17]([C:22]([F:25])([F:23])[F:24])[CH:16]=4

Participants

5

Reactant 2

HCID 962WaterHCID 23000063HCID 23000063, compound

Product 1

HCID 6538749HCID 6538749, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-propenyl)-9-trifluoromethyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one (108 mg, 0.3 mmol) in DMF (6 ml) and H20 (1 ml) was added PdCl2 (6 mg, 0.03 mmol) and CuC12 (48 mg, 0.36 mmol). After stirring the mixture overnight at room temperature it was poured into 30 ml of water and extracted with ethyl acetate (50 ml X 3). The organic layers were combined, washed with water (10 ml×3) and dried over NaSO4. Evaporation of the solution yielded a residue, which was purified by flash chromatography (ethyl acetate: petrol ether=70:30) to yield 78 mg of 2-(2-oxopropyl)-9-trifluoromethyl-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one (69%), mp295-297° C. (ethanol); IR 3310, 1710, 1650, 1310, 800 cm−1; 1H NMR (400 MHz) 2.20 (s 3 H), 3.58 (s, 2 H), 3.78 (s, 2 H), 7.18-7.30 (m, 2 H), 7.46 (d, J=8.6 Hz, 1 H), 7.57 (s, 1 H), 7.61 (d, J=8.1 Hz, 1 H), 8.13 (s, 1 H), 10.14 (s, 1 H), 12.07 (s, 1 H); 13C NMR (100 MHz) 29.5, 31.2, 49.9, 108.4, 112.1, 115.8, (q, J. 3 Hz), 118.3 (q 3 Hz), 120.0 (q, J=37 Hz), 122.0, 122.3, 125.5 (q, J=270 Hz), 125.8, 127.8, 130.0, 130.3, 134.3, 134.5, 138.7, 171.3, 205.9; Anal. (C2OH15N2O2F3, 372.346): calcd. C, 64.51; H 4.06; N, 7.52; found C 64.30; H, 4.23; N, 7.50

Workup

  1. extractionextracted with ethyl acetate (50 ml X 3)
  2. washwashed with water (10 ml×3)
  3. dry with materialdried over NaSO4
  4. customEvaporation of the solution
  5. customyielded a residue, which
  6. customwas purified by flash chromatography (ethyl acetate: petrol ether=70:30)

Sources & evidence

ORD record
ord-ea9417a38a3644adbf9d1e7fe4a44a3c
Source dataset
uspto-grants-2003_08
Patent number
US06610684B2

Reaction notes

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