4-Cyano-2-Fluorophenylboronic Acid → 5-(4-Cyano-2-fluoro-phenyl)-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

HRID 2406349Notes

Reaction equation

HRID 2406349 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.[C:26]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[C:30]([F:37])[CH:29]=1)#[N:27]>>[C:26]([C:28]1[CH:33]=[CH:32][C:31]([C:2]2[CH:3]=[C:4]3[CH2:25][C:9]4([CH2:10][C:11]5([CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:15][CH2:16]5)[CH2:24]4)[O:8][C:5]3=[CH:6][N:7]=2)=[C:30]([F:37])[CH:29]=1)#[N:27]

Participants

3

Reactant 2

HCID 447552094-Cyano-2-Fluorophenylboronic AcidHCID 867012005-Chloro-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Product 1

HCID 867012095-(4-Cyano-2-fluoro-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 4-cyano-2-fluoro-phenylboronic acid following a procedure analogous to that described for Example 1; the reaction is conducted in a microwave oven at 140° C. LC (method 3): tR=1.16 min; Mass spectrum (ESI+): m/z=450 [M+H]+.

Workup

  1. customthe reaction is conducted in a microwave oven at 140° C

Sources & evidence

ORD record
ord-9e2887bf370e40f797ce299dd52ad735
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Reaction notes

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