Sodium Carbonate → tert-Butyl 4-[(2-{4-[5-chloro-2-(trifluoromethoxy)phenyl]-2-oxopyridin-1(2H)-yl}-3-cyclopropylpropanoyl)amino]benzoate

HRID 56668Notes

Reaction equation

HRID 56668 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([CH:8]([CH2:25][CH:26]2[CH2:28][CH2:27]2)[C:9]([NH:11][C:12]2[CH:24]=[CH:23][C:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:14][CH:13]=2)=[O:10])[C:4](=[O:29])[CH:3]=1.[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([O:40][C:41]([F:44])([F:43])[F:42])=[C:35](B(O)O)[CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([O:40][C:41]([F:42])([F:43])[F:44])=[C:35]([C:2]2[CH:7]=[CH:6][N:5]([CH:8]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[C:9]([NH:11][C:12]3[CH:13]=[CH:14][C:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:23][CH:24]=3)=[O:10])[C:4](=[O:29])[CH:3]=2)[CH:36]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 53216719(5-Chloro-2-(trifluoromethoxy)phenyl)boronic acidHCID 117622557tert-Butyl 4-{[2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-cyclopropylpropanoyl]amino}benzoate

Product 1

HCID 117622699tert-Butyl 4-[(2-{4-[5-chloro-2-(trifluoromethoxy)phenyl]-2-oxopyridin-1(2H)-yl}-3-cyclopropylpropanoyl)amino]benzoate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

110 mg (purity 80%, 0.19 mmol) of tert-butyl 4-{[2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-cyclopropylpropanoyl]amino}benzoate (racemate), 46 mg (0.19 mmol) of 5-chloro-2-trifluoromethoxyphenylboronic acid and 22 mg (0.02 mmol) of tetrakis(triphenylphosphine)palladium(0) were taken up in 2.5 ml of dioxane and 2.5 ml of saturated aqueous sodium carbonate solution and irradiated in a microwave at 130° C. for 12 min. The crude product was purified by flash chromatography (silica gel 60, cyclohexane/ethyl acetate mixtures). Yield: 77 mg (purity 92%, 64% of theory)

Workup

  1. customThe crude product was purified by flash chromatography (silica gel 60, cyclohexane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-707458a3ee36445a8321df393984a253
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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