(4-Bromophenyl)boronic acid → 3-(4-{[1-(4-Bromophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl]methoxy}-2,3-difluorophenyl)propan-1-ol

HRID 2167376Notes

Reaction equation

HRID 2167376 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:7]=[CH:6][NH:5][C:4]=1[C:8]([O:10][CH3:11])=O.[Br:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.[F:24][C:25]1[C:30]([F:31])=C(O)[CH:28]=[CH:27][C:26]=1[CH2:33][CH2:34][C:35](OCC)=[O:36]>>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([N:5]2[CH:6]=[CH:7][C:3]([C:2]([F:13])([F:12])[F:1])=[C:4]2[CH2:8][O:10][C:11]2[CH:28]=[CH:27][C:26]([CH2:33][CH2:34][CH2:35][OH:36])=[C:25]([F:24])[C:30]=2[F:31])=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 79599(4-Bromophenyl)boronic acidHCID 90404786Ethyl 3-(2,3-difluoro-4-hydroxyphenyl)propanoateHCID 90405535methyl 3-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 904058613-(4-{[1-(4-Bromophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl]methoxy}-2,3-difluorophenyl)propan-1-ol

Procedure

The title compound was prepared by (a) reacting the product prepared in Step B of Example 1 and 4-bromophenylboronic acid according to the procedure described in Example 1, Step C, (b) then reacting the resulting product according to the procedure in Example 1, Step D, (c) then reacting the resulting product with ethyl 3-(2,3-difluoro-4-hydroxyphenyl)propanoate according to the procedure described in Example 1, Step E, and Example 2.

Sources & evidence

ORD record
ord-208e35e9ded34389b9ed4e3e9af07aad
Source dataset
uspto-grants-2015_06
Patent number
US09045454B2

Reaction notes

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