Bromomethylcyclopropane → 3-{4-[2-(4-Chloro-2-cyclopropylmethoxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-phenyl}-propionic acid methyl ester

HRID 1875799Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:16][CH:15]=3)[C:11]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:10]=3[N:9]=2)=[C:4]([O:31][CH2:32][CH:33]2CC[CH2:35][CH2:34]2)[CH:3]=1.Br[CH2:39]C1CC1>>[CH3:39][O:24][C:22](=[O:23])[CH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:12]2[C:11]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:10]=3[N:9]=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[O:31][CH2:32][CH:33]2[CH2:35][CH2:34]2)=[CH:15][CH:16]=1

Participants

Reactant 2

HCID 81503Bromomethylcyclopropane

HCID 582092583-{4-[2-(4-Chloro-2-cyclopentylmethoxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-phenyl}-propionic acid2×

Product 1

HCID 670501053-{4-[2-(4-Chloro-2-cyclopropylmethoxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-phenyl}-propionic acid methyl ester

Procedure

The title compound was prepared in analogy to Example 19, from 3-{4-[2-(4-chloro-2-hydroxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-phenyl}-propionic acid methyl ester (Example 59, intermediate b) and bromomethyl-cyclopropane (CAS Reg. No. 7051-34-5). Brown solid (54%). MS (Turbo Spray): m/z=511.2 (M+H).

Sources & evidence

ORD record: ord-bdec1b8574af4a55971d3e4cd7a1421a
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309581B2

Reaction notes

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