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

HRID 2167377Notes

Reaction equation

HRID 2167377 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.[CH3:24][C:25]1[C:30](C)=[C:29](O)[CH:28]=[CH:27][C:26]=1[CH2:33][CH2:34][C:35]([O:37]CC)=[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][C:35]([OH:37])=[O:36])=[C:25]([CH3:24])[C:30]=2[CH3:29])=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 79599(4-Bromophenyl)boronic acidHCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 90405535methyl 3-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 904062163-(4-{[1-(4-Bromophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl]methoxy}-2,3-dimethylphenyl)propanoic acid

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, and (c) then reacting the resulting product with ethyl 3-(2,3-dimethyl-4-hydroxyphenyl)propanoate according to the procedures described in Example 1, Steps E and F.

Sources & evidence

ORD record
ord-2f909d6357754b31a353e46defd5d3d3
Source dataset
uspto-grants-2015_06
Patent number
US09045454B2

Reaction notes

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