Water → HCID 10670191, compound

HRID 989208Notes

Reaction equation

HRID 989208 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 moles) 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 recrystallisation from ethyl acetate/60-80 petrol gave the title compound (E35) (0.2 g, 65%) mp. 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
  7. customfollowed by flash chromatography on silica gel eluting with 3-7% MeOH/CH2Cl2 and recrystallisation from ethyl acetate/60-80 petrol

Sources & evidence

ORD record
ord-681dfcda6b154a33b6b7f067d2e49713
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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