2,4-Difluorophenylboronic acid → [4-(2-Azepan-1-yl-ethoxy)-phenyl]-[2-(2,4-difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-methanone

HRID 1513959Notes

Reaction equation

HRID 1513959 reaction equation
[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:38]=[CH:37][C:14]([C:15]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=4)[CH:20]=[CH:19][C:18]=3OS(C(F)(F)F)(=O)=O)=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:39][C:40]1[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:41]=1B(O)O.FC1C=C(F)C=CC=1C1C=CC2C(=CC=C(OC)C=2)C=1C(C1C=CC(OCCN2CCCCC2)=CC=1)=O>>[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=4)[CH:20]=[CH:19][C:18]=3[C:41]3[CH:42]=[CH:43][C:44]([F:46])=[CH:45][C:40]=3[F:39])=[O:16])=[CH:37][CH:38]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 27343342,4-Difluorophenylboronic acidHCID 57552509Trifluoromethanesulfonic acid 1-[4-(2-azepan-1-yl-ethoxy)-benzoyl]-6-methoxynaphthalen-2-yl esterHCID 57552512[2-(2,4-Difluoro-phenyl)-6-methoxynaphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Product 1

HCID 11466453[4-(2-Azepan-1-yl-ethoxy)-phenyl]-[2-(2,4-difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-methanoneYield 85.3%

Procedure

Couple trifluoromethanesulfonic acid 1-[4-(2-azepan-1-yl-ethoxy)-benzoyl]-6-methoxynaphthalen-2-yl ester (1.4 g, 2.5 mmol) and 2,4-difluorophenyl boronic acid (1.2 g, 7.6 mmol) by the procedure used to prepare [2-(2,4-difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone to give yields 1.1 g (85%) of the title compound: mass spectrum (ion spray) m/z=516.3 (M+H).

Workup

  1. customto give

Sources & evidence

ORD record
ord-fc64d6ba700a4a38bafec0d2b7eaebc1
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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