Potassium Carbonate → HCID 57656071, compound

HRID 911415Notes

Reaction equation

[C:1](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.Br[C:17]1[CH:33]=[CH:32][C:20]2[CH2:21][CH2:22][N:23]([C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[CH2:24][CH2:25][C:19]=2[C:18]=1[O:34][CH3:35]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:35][O:34][C:18]1[C:19]2[CH2:25][CH2:24][N:23]([C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[CH2:22][CH2:21][C:20]=2[CH:32]=[CH:33][C:17]=1[CH3:1]

Participants

Conditions

Temperature: 115 °C

Procedure

Add potassium carbonate (5.65 g, 40.91 mmol), tetrakis(triphenylphosphine)palladium (1.576 g, 1.363 mmol) and trimethylboroxine (2.053 g, 2.3 mL, 16.35 mmol) to a solution of 7-bromo-6-methoxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (4.8 g, 13.63 mmol) in dimethylformamide (40 mL) under nitrogen. Heat the mixture to 115° C. for 6 h. Add water and extract the aqueous phase twice with EtOAc. Combine the organic extracts, dry over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 19:1) to obtain the desired intermediate as a solid (3.23 g, 83%). GC-MS m/z 287 (M+).

Workup

extractionAdd water and extract the aqueous phase twice with EtOAc
dry with materialdry over Na2SO4
filtrationfilter
concentrationconcentrate in vacuo
customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 19:1)

Sources & evidence

ORD record: ord-880e8baa506d4683b62fcf5e7acf7077
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022062B2

Reaction notes

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