Water → HCID 59494348, compound

HRID 872038Notes

Reaction equation

HRID 872038 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[N:14]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:15]=[C:16]([CH2:17][N:18]([CH:26]3[CH2:28][CH2:27]3)[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:9]=12.O.O1[CH2:40][CH2:39]OCC1>Cl[Pd]Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH:26]1([N:18]([CH2:17][C:16]2[C:9]3[C:10](=[N:11][CH:12]=[CH:13][C:8]=3[C:39]([CH3:40])=[CH2:1])[N:14]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:15]=2)[C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 86645635HCID 86645635, compound

Product 1

HCID 59494348HCID 59494348, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
110 °C

Procedure

Potassium carbonate (207 mg), isopropenylboric acid pinacol ester (228 μl) and bis(diphenylphosphino)ferrocene dichloropalladium(II) (36.6 mg) were added to a solution of tert-butyl {[4-bromo-1-(3-methoxypropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl}cyclopropylcarbamate (219 mg) in 1,4-dioxane (14.5 ml) and the mixture was stirred under argon atmosphere at 110° C. for 19 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=6/1 to 3/7) to give tert-butyl cyclopropyl{[4-isopropenyl-1-(3-methoxypropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl}carbamate (173 mg) as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=6/1 to 3/7)

Sources & evidence

ORD record
ord-d5864cc2378e4d09963e6751fa487156
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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