Triethylamine → 1-(2,6-difluorophenyl)-7-[(2,4-difluorophenyl)ethynyl]-2H-quinolizin-2-one

HRID 1454981Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:9]2[N:4]([CH:5]=[CH:6][C:7](=[O:20])[C:8]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[CH:3]=1.[C:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[F:30])#[CH:22].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.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.[Cu]I>[F:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([F:18])[C:12]=1[C:8]1[C:7](=[O:20])[CH:6]=[CH:5][N:4]2[C:9]=1[CH:10]=[CH:11][C:2]([C:22]#[C:21][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[F:30])=[CH:3]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 7-bromo-1-(2,6-difluorophenyl)-2H-quinolizin-2-one (100 mg) was added 1ethynyl-2,4-difluorobenzene (82 mg), triethylamine (0.17 ml), dichlorobis(triphenylphosphine)palladium (25 mg), CuI (6 mg) in DMF was heated to 100° C. until reaction complete. The mixture was diluted with ethyl acetate, washed with water (4×), brine, dried over MgSO4, and concentrated to yield crude material. The crude material was purified by silica gel chromatography (100% ethyl acetate) to yield the title compound.

Workup

washwashed with water (4×), brine
dry with materialdried over MgSO4
concentrationconcentrated
customto yield crude material
customThe crude material was purified by silica gel chromatography (100% ethyl acetate)

Sources & evidence

ORD record: ord-f3750d6a8b094c95ac2f642c92f69bfd
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482345B2

Reaction notes

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