(2,2-Dimethyl-2,3-dihydro-1-benzofuran-5-yl)boronic acid → 4'-{[5-(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-4-ethyl-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile

HRID 1674403Notes

Reaction equation

HRID 1674403 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:6][C:5]2[CH:7]=[C:8](B(O)O)[CH:9]=[CH:10][C:4]=2[O:3]1.Br[C:16]1[C:21](=[O:22])[N:20]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:26][CH:25]=2)[C:19]([CH2:38][CH2:39][CH3:40])=[N:18][C:17]=1[CH2:41][CH3:42]>O1CCOCC1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][C:2]1([CH3:14])[CH2:6][C:5]2[CH:7]=[C:8]([C:16]3[C:21](=[O:22])[N:20]([CH2:23][C:24]4[CH:25]=[CH:26][C:27]([C:30]5[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:28][CH:29]=4)[C:19]([CH2:38][CH2:39][CH3:40])=[N:18][C:17]=3[CH2:41][CH3:42])[CH:9]=[CH:10][C:4]=2[O:3]1

Participants

7

Reactant 2

HCID 23005350(2,2-Dimethyl-2,3-dihydro-1-benzofuran-5-yl)boronic acidHCID 574600664'-[(5-bromo-4-ethyl-6-oxo-2-propylpyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrile

Product 1

HCID 594693844'-{[5-(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-4-ethyl-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrileYield 100.5%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 10796Cesium carbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)boronic acid (0.33 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (0.05 g) and 4′-[(5-bromo-4-ethyl-6-oxo-2-propylpyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrile (0.5 g) in 1,4-dioxane (10 mL) and 2 M cesium carbonate (2 mL) was stirred overnight at 100° C. under an argon atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.58 g, 100%).

Workup

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2dec5ab83e2e4123b09af5ba43d8799d
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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