Ethyl Acetate → HCID 86618288, compound

HRID 2264583Notes

Reaction equation

HRID 2264583 reaction equation
B(Br)(Br)Br.[F:5][C:6]([F:38])([F:37])[C:7]1[CH:8]=[C:9]([NH:21][C:22]([N:24]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]3[CH:31]=[C:32]([O:35]C)[CH:33]=[CH:34][C:25]2=3)=[O:23])[CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>C(=O)=O.CC(C)=O.C(Cl)Cl>[F:37][C:6]([F:5])([F:38])[C:7]1[CH:8]=[C:9]([NH:21][C:22]([N:24]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]3[CH:31]=[C:32]([OH:35])[CH:33]=[CH:34][C:25]2=3)=[O:23])[CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 86618289HCID 86618289, compound

Product 1

HCID 86618288HCID 86618288, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 280Carbon DioxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 38 ml BBr3 (1 M in CH2Cl2) is cooled in dry ice and acetone. Then 1.828 g (3.8 mMol) of 7-methoxy-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid [3-trifluoromethyl-4-(4-methylpiperazin-1-ylmethyl)-phenyl]-amide in 20 ml CH2Cl2 are added dropwise. The mixture is stirred for 90 min at −78° C., warmed up (−40 to −30° C.) and then stirred at this temperature for 3.5 h. The solution is poured into a mixture of 300 g ice, 150 ml sat. Na2CO3 solution and 200 ml EtOAc, the aqueous phase separated off and extracted twice with EtOAc. The organic layers are washed with water (2×) and brine, dried (Na2SO4) and concentrated after addition of 15 g SiO2. The resulting powder is put on top of a SiO2 chromatography column. Eluation with EtOAC/EtOH 19:1→EtOAC/EtOH/Et3N 90:10:1 gives the title compound: MS: [M+1]+=463; Anal.: C,H,N,F.

Workup

  1. temperaturewarmed up (−40 to −30° C.)
  2. stirringstirred at this temperature for 3.5 h
  3. customthe aqueous phase separated off
  4. extractionextracted twice with EtOAc
  5. washThe organic layers are washed with water (2×) and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. additionafter addition of 15 g SiO2

Sources & evidence

ORD record
ord-5fa9c4a949c34e42879fe2c4fb0a508e
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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