Water → HCID 66845094, compound

HRID 253132Notes

Reaction equation

HRID 253132 reaction equation
Br[C:2]1[CH:7]([O:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[NH:6][CH:5]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:3]=1.[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.O>COCCOC.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.[Fe+2].Cl[Pd]Cl>[CH:9]1([O:8][C:7]2[C:2]([C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)=[CH:3][C:4]([C:14]([O:16][CH3:17])=[O:15])=[CH:5][N:6]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 962WaterHCID 2734379(Pyridin-4-yl)boronic acidHCID 66845805HCID 66845805, compound

Product 1

HCID 66845094HCID 66845094, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 5-bromo-6-(cyclopentyloxy)-1,6-dihydropyridine-3-carboxylate (2.50 g, 7.94 mmol) was dissolved in DME (10 mL) and pyridin-4-ylboronic acid (813 mg, 6.61 mmol), DPPF-PdCl2 (108 mg, 0.13 mmol, Strem) and water (0.5 mL, 28 mmol) were added. The mixture was stirred at 40° C. for 4 h. The reaction mixture was cooled to RT, diluted with H1O and extracted 3× with EtOAc. The combined organic extracts were washed 1× with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (40 g pre-packed column, elution 0-30% EtOAc:hexanes) to give the title compound (608 mg, 31%). MS m/z: 299 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. additiondiluted with H1O
  3. extractionextracted 3× with EtOAc
  4. washThe combined organic extracts were washed 1× with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by silica gel chromatography (40 g pre-packed column, elution 0-30% EtOAc:hexanes)

Sources & evidence

ORD record
ord-3cd00afe56d74214821e8ced855600f1
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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