2-(Bromomethyl)-4'-chloro-4-methoxy-1,1'-biphenyl → Methyl (2E)-3-(2-{4-[(4'-chloro-4-methoxy-1,1'-biphenyl-2-yl)methoxy]phenyl}-1-cyclohexyl-1H-imidazol-4-yl)-2-propenoate

HRID 2216534Notes

Reaction equation

HRID 2216534 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:10]=[C:11](/[CH:13]=[C:14](\C)/[C:15]([O:17][CH3:18])=[O:16])[N:12]=2)=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[CH2:41]Br)=[CH:29][CH:28]=1>>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[CH2:41][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:9]([CH:20]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]4)[CH:10]=[C:11](/[CH:13]=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])[N:12]=3)=[CH:4][CH:3]=2)=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 219433382-(Bromomethyl)-4'-chloro-4-methoxy-1,1'-biphenylHCID 136341818Methyl (2E)-3-{2-[4-(hydroxy)phenyl]-1-cyclohexyl-1H-imidazol-4-yl}-2-methyl-2-propenoate

Product 1

HCID 11341937Methyl (2E)-3-(2-{4-[(4'-chloro-4-methoxy-1,1'-biphenyl-2-yl)methoxy]phenyl}-1-cyclohexyl-1H-imidazol-4-yl)-2-propenoateYield 73.2%

Procedure

According to the procedure for preparation of 4.4, phenol 12.9 (60 mg, 0.184 mmol) was alkylated with (4′-chloro-4-methoxy-1,1′-biphenyl-2-yl)methyl bromide (63 mg, 0.202 mmol), to yield 75 mg (73%) of 12.10. MS (ESI) 557.4 (MH+).

Sources & evidence

ORD record
ord-ee5eae4a1b084888b1ba8fc351c0edeb
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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