Potassium Carbonate → HCID 57656071, compound

HRID 2041298Notes

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-d70fb5a02ac04bdea7f3c200feb7203d
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580780B2

Reaction notes

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