Furan-3-boronic acid → cis-2,2,2-Trifluoro-1-(6-furan-3-yl-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-ethanone

HRID 455368Notes

Reaction equation

HRID 455368 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]([N:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]2[C:11]3[CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:15][C:16]=3[CH2:17][C@H:6]12)=[O:4].[O:28]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29]1>>[F:1][C:2]([F:27])([F:26])[C:3]([N:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]2[C:11]3[CH:12]=[C:13]([C:30]4[CH:31]=[CH:32][O:28][CH:29]=4)[CH:14]=[CH:15][C:16]=3[CH2:17][C@H:6]12)=[O:4]

Participants

3

Reactant 2

HCID 2734358Furan-3-boronic acidHCID 58294405trifluoro-methanesulfonic acid cis-1-(2,2,2-trifluoro-acetyl)-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-6-yl ester

Product 1

HCID 58294656cis-2,2,2-Trifluoro-1-(6-furan-3-yl-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-ethanoneYield 61%

Procedure

The title compound is prepared from trifluoro-methanesulfonic acid cis-1-(2,2,2-trifluoro-acetyl)-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-6-yl ester and furan-3-yl-boronic acid following a procedure analogous to that described in Step 2 of Intermediates 17 and 18. Yield: 61% of theory; LC (method 1): tR=4.60 min; Mass spectrum (ESI+): m/z=336 [M+H]+.

Sources & evidence

ORD record
ord-2817c7f54d6245b3a5d6914f877cd51d
Source dataset
uspto-grants-2013_07
Patent number
US08497281B2

Reaction notes

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