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

HRID 2167373Notes

Reaction equation

HRID 2167373 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]([CH3:31])=[C:29]([OH:32])[CH:28]=[CH:27][C:26]=1[CH2:33][CH2:34]C(OCC)=O>>[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:34]=[CH:33][C:26]([CH2:27][CH2:28][CH2:29][OH:32])=[C:25]([CH3:24])[C:30]=2[CH3:31])=[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 904065883-(4-{[1-(4-Bromophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl]methoxy}-2,3-dimethylphenyl)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-dimethyl-4-hydroxyphenyl)propanoate according to the procedure in Example 1, Step E, and Example 2.

Sources & evidence

ORD record
ord-1b5f96bf2ccd4bf994f35e434743af6a
Source dataset
uspto-grants-2015_06
Patent number
US09045454B2

Reaction notes

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