2-Fluoro-4-(methylsulphonyl)benzeneboronic acid → 5-(2-Fluoro-4-methylsulfonyl-phenyl)-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

HRID 2406339Notes

Reaction equation

HRID 2406339 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[CH2:25][C:9]3([CH2:24][C:11]4([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]4)[CH2:10]3)[O:8][C:5]2=[CH:6][N:7]=1.[F:26][C:27]1[CH:32]=[C:31]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:30]=[CH:29][C:28]=1B(O)O>>[F:26][C:27]1[CH:32]=[C:31]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:30]=[CH:29][C:28]=1[C:2]1[CH:3]=[C:4]2[CH2:25][C:9]3([CH2:24][C:11]4([CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[CH2:15][CH2:16]4)[CH2:10]3)[O:8][C:5]2=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 447176662-Fluoro-4-(methylsulphonyl)benzeneboronic acidHCID 867012005-Chloro-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Product 1

HCID 721948515-(2-Fluoro-4-methylsulfonyl-phenyl)-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Procedure

The title compound is prepared from 5-chloro-1″-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] and 2-fluoro-4-methylsulfonyl-phenylboronic acid following a procedure analogous to that described for Example 2; PdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex is the preferred catalyst used. LC (method 1): tR=1.30 min; Mass spectrum (ESI+): m/z=503 [M+H]+.

Sources & evidence

ORD record
ord-0415b58524f046688c01db62e607ed74
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Reaction notes

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