Sodium Carbonate → HCID 86622787, compound

HRID 1965987Notes

Reaction equation

HRID 1965987 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][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]=1OS(C(F)(F)F)(=O)=O.[CH:27]1([C:32]([NH:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=2)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[CH:17][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[C:39]1[CH:40]=[CH:41][C:36]([CH2:35][NH:34][C:32]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:33])=[CH:37][CH:38]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 59787407(4-{[(Cyclopentanecarbonyl)amino]methyl}phenyl)boronic acid

Product 1

HCID 86622787HCID 86622787, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

Dissolve 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (425 mg, 1 mmol), bis(triphenylphosphine)-palladium(II) chloride (0.1 equiv.), 4-[(cyclopentanecarbonyl-amino)-methyl]-phenyl-boronic acid (490 mg, 2.0 mmol) and sodium carbonate (2 equiv.) in THF/water (2:1, 15 mL) and heat the mixture at 80° C. for 6 h. Cool the reaction mixture to ambient temperature, dilute with EtOAc and wash with water. Dry the organic fraction over MgSO4, filter and concentrate in vacuo to obtain 7-chloro-6-{4-[(cyclopentanecarbonyl-amino)-methyl]-phenyl}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine, suitable for use without further purification.

Workup

  1. temperatureCool the reaction mixture to ambient temperature
  2. washwash with water
  3. dry with materialDry the organic fraction over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-7c5d6abad714425586ef4c706bdcf721
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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