Ethyl Acetate → HCID 66602898, compound

HRID 604170Notes

Reaction equation

HRID 604170 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:45]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:47]=1)[CH2:6][N:7]([CH2:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[CH:28][C:27]=1B1OC(C)(C)C(C)(C)O1)[C:8]1[N:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:10][N:9]=1)#[N:2].Br[C:53]1[C:58]([O:59][CH3:60])=[CH:57][CH:56]=[C:55]([C:61]([CH3:63])=[CH2:62])[N:54]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>O1CCOCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:45]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:47]=1)[CH2:6][N:7]([CH2:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[CH:28][C:27]=1[C:53]1[C:58]([O:59][CH3:60])=[CH:57][CH:56]=[C:55]([C:61]([CH3:63])=[CH2:62])[N:54]=1)[C:8]1[N:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])=[CH:10][N:9]=1)#[N:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 59135100HCID 59135100, compoundHCID 66603399HCID 66603399, compound

Product 1

HCID 66602898HCID 66602898, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Tert-butyl 4-(2-{(3-cyano-5-trifluoromethyl-benzyl)-[4,5-dimethoxy-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-amino}-pyrimidin-5-yloxy)-butyrate (60 mg) is dissolved in 1,4-dioxane (1.5 ml) and thereto are added 2-bromo-6-isopropenyl-3-methoxy-pyridine (38 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (7 mg) and cesium carbonate (55 mg), and the mixture is stirred under nitrogen atmosphere at 80° C. overnight. The reaction solution is cooled to room temperature, and thereto are added ethyl acetate and water, and the mixture is separated and the organic layer is filtered by NH— silica gel and the mixture is extracted with ethyl acetate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=85:15→70:30) to give tert-butyl 4-(2-{(3-cyano-5-trifluoromethyl-benzyl)-[2-(6-isopropenyl-3-methoxy-pyridin-2-yl)-4,5-dimethoxy-benzyl]-amino}-pyrimidin-5-yloxy)-butyrate (17 mg). MS (m/z): 734 [M+H]+

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. customthe mixture is separated
  3. filtrationthe organic layer is filtered by NH— silica gel
  4. extractionthe mixture is extracted with ethyl acetate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=85:15→70:30)

Sources & evidence

ORD record
ord-88c36ba8e0de4fb08972dbb7f0adc86c
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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