8-(2,2,2-Trifluoroacetyl)-8-azabicyclo[3.2.1]octan-3-one → 1-[3-(3-Bromo-5-methoxy-xanthen-9-ylidene)-8-aza-bicyclo[3.2.1]oct-8-yl]-2,2,2-trifluoro-ethanone

HRID 733413Notes

Reaction equation

HRID 733413 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=O)[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[C:11]([O:16][CH3:17])[CH:10]=[CH:9][CH:8]=3.C(N(CC)C(C1C=CC2C(=O)C3C(OC=2C=1)=CC=CC=3)=O)C.[F:41][C:42]([F:55])([F:54])[C:43]([N:45]1[CH:50]2[CH2:51][CH2:52][CH:46]1[CH2:47][C:48](=O)[CH2:49]2)=[O:44]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[C:48]3[CH2:47][CH:46]4[N:45]([C:43](=[O:44])[C:42]([F:54])([F:41])[F:55])[CH:50]([CH2:51][CH2:52]4)[CH2:49]3)[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[C:11]([O:16][CH3:17])[CH:10]=[CH:9][CH:8]=3

Participants

4

Reactant 3

HCID 152523068-(2,2,2-Trifluoroacetyl)-8-azabicyclo[3.2.1]octan-3-oneHCID 15953972N,N-Diethyl-9-oxo-9H-xanthene-3-carboxamide2×HCID 574366693-Bromo-5-methoxy-xanthen-9-one

Product 1

HCID 577253491-[3-(3-Bromo-5-methoxy-xanthen-9-ylidene)-8-aza-bicyclo[3.2.1]oct-8-yl]-2,2,2-trifluoro-ethanone

Procedure

Using an adaptation of the method described in Procedure 7, substituting 3-bromo-5-methoxy-xanthen-9-one, 3k for 9-oxo-9H-xanthene-3-carboxylic acid diethylamide, 6a and 8-(2,2,2-trifluoro-acetyl)-8-aza-bicyclo[3.2.1]octan-3-one for N-carbethoxynortropinone, the title compound 1-[3-(3-bromo-5-methoxy-xanthen-9-ylidene)-8-aza-bicyclo[3.2.1]oct-8-yl]-2,2,2-trifluoro-ethanone, 4k was obtained. MS m/z (MH+) 467.7, 469.7.

Sources & evidence

ORD record
ord-c7a5645c0dc846fd9a5ad60774b13589
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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