Potassium Carbonate → HCID 86629594, compound

HRID 2041114Notes

Reaction equation

HRID 2041114 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([F:19])[C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[OH:20].C(=O)([O-])[O-].[K+].[K+].[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1>CN(C=O)C.CCOCC>[Cl:1][C:2]1[CH:18]=[C:17]([F:19])[C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])[CH2:9][CH2:10][C:4]=2[C:3]=1[O:20][CH2:32][C:31]1[CH:34]=[CH:35][C:28]([F:27])=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 57656106HCID 57656106, compound

Product 1

HCID 86629594HCID 86629594, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Dissolve 7-chloro-9-fluoro-6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.25 g, 0.8 mmol) in DMF (8 mL), add potassium carbonate (0.56 g, 4.0 mmol) and 4-fluorobenzyl bromide (0.46 mL, 2.4 mmol). After 14 h at 90° C., dilute with ether and wash with brine. Dry the organic layer over Na2SO4 and evaporate onto silica gel. Purify by chromatography on silica gel eluting with EtOAc/hexane (0:1 to 1:0) to obtain 7-chloro-9-fluoro-6-(4-fluorobenzyloxy)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine.

Workup

  1. washwash with brine
  2. dry with materialDry the organic layer over Na2SO4
  3. customevaporate onto silica gel
  4. customPurify by chromatography on silica gel eluting with EtOAc/hexane (0:1 to 1:0)

Sources & evidence

ORD record
ord-1a5440f8dad4489cbe07e6b43ead7047
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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