Methanol → HCID 131732879, compound

HRID 526441Notes

Reaction equation

HRID 526441 reaction equation
Br[C:2]1[C:3]([CH3:30])=[CH:4][C:5]([N:8]2[C:12]([O:13][CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[C:11]([C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=3)[CH:10]=[N:9]2)=[N:6][CH:7]=1.CN([CH:34]=[O:35])C.[CH3:36][OH:37].C(N(CC)CC)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].O>[C:26]([C:25]1[CH:28]=[CH:29][C:22]([C:11]2[CH:10]=[N:9][N:8]([C:5]3[CH:4]=[C:3]([CH3:30])[C:2]([C:36]([O:35][CH3:34])=[O:37])=[CH:7][N:6]=3)[C:12]=2[O:13][CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:23][CH:24]=1)#[N:27]

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 131732880HCID 131732880, compound

Product 1

HCID 131732879HCID 131732879, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Combined 4-(1-(5-bromo-4-methylpyridin-2-yl)-5-((2-(trimethylsilyl)ethoxy)methoxy)-1H-pyrazol-4-yl)benzonitrile (10.0 g, 20.66 mmol), DMF (60 mL) and MeOH (60 mL) then added triethylamine (6.26 g, 61.98 mmol) and Pd(dppf)Cl2 (756.2 mg, 1.033 mmol). The mixture was stirred at 120° C. under 1 MPa of CO overnight. Then the reaction mixture was evaporated in vacuum to give a residue which was combined with water, filtered, and the aqueous was extracted with EtOAc (100 mL×2). The combined EtOAc layers were washed with brine and dried (Na2SO4), and concentrated to give the title compound (8.67 g).

Workup

  1. customThen the reaction mixture was evaporated in vacuum
  2. customto give a residue which
  3. filtrationfiltered
  4. extractionthe aqueous was extracted with EtOAc (100 mL×2)
  5. washThe combined EtOAc layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0b74c93d0c2b40bcbb4c14493690dc11
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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