Water → HCID 59494734, compound

HRID 872032Notes

Reaction equation

HRID 872032 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[C:7]1(B(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.Br[C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[C:20]([CH2:32][N:33]([CH:41]1[CH2:43][CH2:42]1)[C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=N[N:22]2[CH2:27][CH2:28][CH2:29][O:30][CH3:31]>ClCCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:41]1([N:33]([CH2:32][C:20]2[C:19]3[C:23](=[CH:24][CH:25]=[CH:26][C:18]=3[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:22]([CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:1]=2)[C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:43][CH2:42]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 86645633HCID 86645633, compound

Product 1

HCID 59494734HCID 59494734, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (276 mg), phenylboronic acid (122 mg), dichlorobis(triphenylphosphine)palladium(II) (175 mg) and water (132 μl) were added to a solution of tert-butyl {[4-bromo-1-(3-methoxypropyl)-1H-indazol-3-yl]methyl}cyclopropylcarbamate (218 mg) in 1,2-dichloroethane (11 ml) and the mixture was stirred under argon atmosphere at 80° C. for 1.5 hours. The reaction mixture was cooled to room temperature, poured into ice water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine, 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=20/1 to 7/3) to give tert-butyl cyclopropyl{[1-(3-methoxypropyl)-4-phenyl-1H-indol-3-yl]methyl}carbamate (212 mg) as a 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
  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=20/1 to 7/3)

Sources & evidence

ORD record
ord-bd6bd410592d4d03bb771be72373f372
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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