Water → 3-[4-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-3-trifluoromethoxy-phenyl]-acrylic acid tert-butyl ester

HRID 883070Notes

Reaction equation

HRID 883070 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[CH:2]=[CH2:3].Br[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:26]=[C:25]3[C:20]([C:21]([CH3:31])([CH3:30])[CH2:22][C:23](=[O:29])[N:24]3[CH2:27][CH3:28])=[CH:19][C:18]=2[CH3:32])=[C:13]([O:33][C:34]([F:37])([F:36])[F:35])[CH:12]=1.C1(N(C2CCCCC2)C)CCCCC1.O>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:6]([O:5][C:1](=[O:4])[CH:2]=[CH:3][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:26]=[C:25]3[C:20]([C:21]([CH3:31])([CH3:30])[CH2:22][C:23](=[O:29])[N:24]3[CH2:27][CH3:28])=[CH:19][C:18]=2[CH3:32])=[C:13]([O:33][C:34]([F:35])([F:36])[F:37])[CH:12]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 15458tert-Butyl acrylateHCID 24210N-Methyl dicyclohexylamineHCID 686656347-(4-Bromo-2-trifluoromethoxy-phenyl)-1-ethyl-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 686664453-[4-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-3-trifluoromethoxy-phenyl]-acrylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A sealed tube was charged with Pd[P(tBu)3]2 (4 mg, 0.0075 mmol), tert-butyl acrylate (0.03 mL, 0.18 mmol) and Compound 5B (68 mg, 0.15 mmol) in 1 mL of dry dioxane. To this was added dicyclohexyl methyl amine (0.04 mL, 0.18 mmol) and the tube was sealed and heated to 80° C. overnight. After the reaction was cooled, 3 mL of water was added and the solution was passed through a 5 mL solid phase extraction (SPE) column. The SPE was washed with dichloromethane and the collected eluant was stripped on the roto yap to give crude product Compound 5C which was further purified by flash chromatography (25% EtOAc/Hexane) to yield 45 mg (60%) of product. MS (electrospray): mass calculated for C28H32F3NO4, 503.23; m/z found 504.2 [M+H]+.

Workup

  1. customthe tube was sealed
  2. temperatureAfter the reaction was cooled
  3. extractionthe solution was passed through a 5 mL solid phase extraction (SPE) column
  4. washThe SPE was washed with dichloromethane

Sources & evidence

ORD record
ord-1c604d093e3c48e6ac991554eb794cb0
Source dataset
uspto-grants-2012_08
Patent number
US08236819B2

Reaction notes

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