3-Chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenol → 1-{4-[3-Chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenoxymethyl]-phenyl}-cyclopropanecarboxylic acid methyl ester

HRID 1095962Notes

Reaction equation

HRID 1095962 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:26])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:25])[C:9]([OH:24])([C:14]1[CH:15]=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]([F:13])([F:12])[F:11].[CH3:27][O:28][C:29]([C:31]1([C:34]2[CH:39]=[CH:38][C:37]([CH2:40]Br)=[CH:36][CH:35]=2)[CH2:33][CH2:32]1)=[O:30]>>[CH3:27][O:28][C:29]([C:31]1([C:34]2[CH:35]=[CH:36][C:37]([CH2:40][O:26][C:4]3[CH:5]=[CH:6][C:7]([CH:8]([CH3:25])[C:9]([OH:24])([C:14]4[CH:15]=[N:16][C:17]5[C:22]([CH:23]=4)=[CH:21][CH:20]=[CH:19][CH:18]=5)[C:10]([F:11])([F:13])[F:12])=[C:2]([Cl:1])[CH:3]=3)=[CH:38][CH:39]=2)[CH2:33][CH2:32]1)=[O:30]

Participants

3

Reactant 2

HCID 574212993-Chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenolHCID 57443306Methyl 1-(4-(bromomethyl)phenyl)cyclopropanecarboxylate

Product 1

HCID 666993861-{4-[3-Chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenoxymethyl]-phenyl}-cyclopropanecarboxylic acid methyl ester

Procedure

In analogy to Example 140, step 6, 3-chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenol (Example 140, step 5) was reacted with 1-(4-bromomethyl-phenyl)-cyclopropanecarboxylic acid methyl ester (CAS 873372-30-6) to give the title compound as an off-white solid. MS (m/e)=570.4 [M+H+].

Sources & evidence

ORD record
ord-f3170fcf2099472fa1bdd7b119972cf2
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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