Ethyl Acetate → 1-[3-(3-Bromo-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]oct-8-yl]-2,2,2-trifluoroethanone

HRID 733408Notes

Reaction equation

HRID 733408 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[C:16]3[CH2:22][CH:21]4[N:23]([C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH:18]([CH2:19][CH2:20]4)[CH2:17]3)[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C(N(CC)C(C1C=CC2C(=C3CC4NC(CC4)C3)C3C(OC=2C=1)=CC=CC=3)=O)C.CCOC(C)=O>CCCCCCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]([CH:16]3[CH2:22][CH:21]4[N:23]([C:24](=[O:29])[C:25]([F:26])([F:28])[F:27])[CH:18]([CH2:19][CH2:20]4)[CH2:17]3)[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 469181419-(8-azabicyclo[3.2.1]octan-3-ylidene)-N,N-diethylxanthene-3-carboxamide2×HCID 577253121-[3-(3-Bromoxanthen-9-ylidene)-8-aza-bicyclo[3.2.1]oct-8-yl]-2,2,2-trifluoroethanone

Product 1

HCID 578392651-[3-(3-Bromo-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]oct-8-yl]-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Using an adaptation of the method described in Procedure 9, substituting 1-[3-(3-bromoxanthen-9-ylidene)-8-aza-bicyclo[3.2.1]oct-8-yl]-2,2,2-trifluoro-ethanone, 1j for 9-(8-aza-bicyclo[3.2.1]oct-3-ylidene)-9H-xanthene-3-carboxylic acid diethylamide, 8a, the title compound 1-[3-(3-bromo-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]oct-8-yl]-2,2,2-trifluoro-ethanone, 2j was obtained after puirification via flash column chromatography (eluent gradient: 5% to 25% EtOAc in heptane). MS m/z (MH+) 465.8.

Sources & evidence

ORD record
ord-e9f860a73aaa4b88929428ea6d1ad73c
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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