Dichloromethane → HCID 67975419, compound

HRID 623882Notes

Reaction equation

C(Cl)Cl.[C:4]([C:7]1[C:8]([CH3:28])=[CH:9][C:10]([C:13]2[CH:27]=[CH:26][C:16]([O:17][CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:14]=2)=[N:11][CH:12]=1)(=[NH:6])[NH2:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][C:37]([C:39]1([C:42]([F:45])([F:44])[F:43])[CH2:41][CH2:40]1)=O>[Cl-].[Na+].O>[CH3:24][C:19]([CH3:25])([CH2:18][O:17][C:16]1[CH:26]=[CH:27][C:13]([C:10]2[CH:9]=[C:8]([CH3:28])[C:7]([C:4]3[NH:5][C:37]([C:39]4([C:42]([F:45])([F:44])[F:43])[CH2:41][CH2:40]4)=[CH:36][N:6]=3)=[CH:12][N:11]=2)=[CH:14][CH:15]=1)[C:20]([O:22][CH3:23])=[O:21]

Participants

Conditions

Temperature: 50 °C

Procedure

To methylene chloride (10 mL) and saturated brine (10 mL) were added methyl 3-[4-(5-carbamimidoyl-4-methylpyridin-2-yl)phenoxy]-2,2-dimethylpropanoate (500 mg) and potassium carbonate (430.3 mg), then, 2-bromo-1-[1-(trifluoromethyl)cyclopropyl]-ethanone (431.6 mg) was added to the mixture, and the resulting mixture was stirred at 50° C. overnight. The organic layer was separated and the residue obtained by concentrating the same under reduced pressure was purified by silica gel column chromatography (n-hexane:ethyl acetate=75:25 to 25:75) to obtain methyl 2,2-dimethyl-3-[4-(4-methyl-5-{5-[1-(trifluoromethyl)cyclopropyl]-1H-imidazol-2-yl}pyridin-2-yl)phenoxy]propanoate (423 mg).

Workup

customThe organic layer was separated
customthe residue obtained
concentrationby concentrating the same under reduced pressure
customwas purified by silica gel column chromatography (n-hexane:ethyl acetate=75:25 to 25:75)

Sources & evidence

ORD record: ord-0eb09358f7a9409da5d2ac7470a64b4d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302996B2

Reaction notes

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