Sodium Carbonate → HCID 86622788, compound

HRID 1965988Notes

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.[F:27][C:28]([F:42])([F:41])[CH2:29][NH:30][CH2:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=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:13])([F:15])[F:14])[CH2:9][CH2:10][C:4]=2[C:3]=1[C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([CH2:31][NH:30][CH2:29][C:28]([F:42])([F:41])[F:27])[CH:33]=1

Participants

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.), 3-[(2,2,2-trifluoroethyl-amino)-methyl]-phenyl-boronic acid (465 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-3-(2,2,2-trifluoroacetyl)-6-{3-[(2,2,2-trifluoroethyl-amino)-methyl]-phenyl}-2,3,4,5-tetrahydro-1H-benzo[d]azepine, suitable for use without further purification.

Workup

temperatureCool the reaction mixture to ambient temperature
washwash with water
dry with materialDry the organic fraction over MgSO4
filtrationfilter
concentrationconcentrate in vacuo

Sources & evidence

ORD record: ord-445f7cdb9c2f4df4b20a3307e7cb08f3
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420631B2

Reaction notes

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