Water → HCID 59494651, compound

HRID 872039Notes

Reaction equation

HRID 872039 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](OB(O)O)[CH3:8].Br[C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[N:20]([CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:21]=[C:22]([CH2:23][N:24]([CH:32]3[CH2:34][CH2:33]3)[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:15]=12.O>O1CCOCC1.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:32]1([N:24]([CH2:23][C:22]2[C:15]3[C:16](=[N:17][CH:18]=[CH:19][C:14]=3[CH2:7][CH3:8])[N:20]([CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:21]=2)[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29])[CH2:33][CH2:34]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 61925Ethyl dihydrogen borateHCID 86645635HCID 86645635, compound

Product 1

HCID 59494651HCID 59494651, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Potassium carbonate (207 mg), ethyl boric acid (92.4 mg) 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 3 hours. The reaction mixture was cooled to room temperature, water was added therein and 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=4/1 to 1/3) to give tert-butyl cyclopropyl{[4-ethyl-1-(3-methoxypropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl}carbamate (119 mg) as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-83ed266e488246d682c035e760e4718c
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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