Water → HCID 10670191, compound

HRID 1603797Notes

Reaction equation

HRID 1603797 reaction equation
Br[C:2]1([O:24][CH3:25])[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:8]2[N:7]([C:15](=[O:23])[NH:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:6][CH2:5][C:4]=2[CH2:3]1.[CH3:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=1B(O)O.O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH3:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=1[C:21]1[CH:22]=[C:17]([NH:16][C:15]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([O:24][CH3:25])=[C:10]([C:11]([F:14])([F:13])[F:12])[CH:9]=3)[CH2:5][CH2:6]2)=[O:23])[CH:18]=[N:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27627114-Methylpyridine-3-Boronic AcidHCID 86588343HCID 86588343, compound

Product 1

HCID 10670191HCID 10670191, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1-[5-Bromo-(3-pyridylcarbamoyl]-5-methoxy-6-trifluoromethylindoline (D26) (0.3 g, 0.7 mmoles) and 4-methyl-3-pyridylboronic acid (0.12 g, 0.9 mmoles) was heated under reflux in dimethoxyethane (80 ml) and water (10 ml) with sodium carbonate (0.15 g, 1.4 mmoles) and palladium tetrakis triphenylphosphine (0.1 g, 12 mole %) under an inert atmosphere for 18 hours. After cooling the mixture was partitioned between ethyl acetate (250 ml) and water (200 ml). The organic layer was separated and washed with saturated sodium chloride solution then dried (Na2SO4). Evaporation of the solvent followed by flash chromatography on silica gel eluting with 3-7% MeOH/CH2Cl2 and recrytallisation from ethyl acetate/60-80 petrol gave the title compound (E35) (0.2 g, 65%) m.p. 125-8° C.

Workup

  1. temperatureAfter cooling the mixture
  2. customwas partitioned between ethyl acetate (250 ml) and water (200 ml)
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialthen dried (Na2SO4)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e112cc56988944e6a90f4918e947329a
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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