Ethanol → 5-(2,3-Difluoro-4-octylphenyl)-2-(6-octyloxypyridin-3-yl)pyrimidine

HRID 376777Notes

Reaction equation

HRID 376777 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[N:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12][CH:13]=2)=[N:6][CH:7]=1.[F:23][C:24]1[C:29]([F:30])=[C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:27]=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:23][C:24]1[C:29]([F:30])=[C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:27]=[CH:26][C:25]=1[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[N:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 193590915-Bromo-2-(6-octyloxypyridin-3-yl)pyrimidineHCID 19359093(2,3-Difluoro-4-octylphenyl)boronic acid

Product 1

HCID 193590965-(2,3-Difluoro-4-octylphenyl)-2-(6-octyloxypyridin-3-yl)pyrimidineYield 84.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The reaction of 3.5 mmol of 5-bromo-2-(6-octyloxypyridin-3-yl)pyrimidine, 3.85 mmol of 2,3-difluoro-4-octylphenylboronic acid, 7 mmol of sodium carbonate and 0.04 mmol of tetrakis(triphenylphosphine)palladium(0) in 20 ml of toluene: 10 ml of ethanol and 10 ml of water it carried out analogously to the procedure indicated for Example 1a). The crude product is separated off by column chromatography on silica gel 60 using heptane/ethyl acetate 9:1 (v/v) as eluent and is recrystallized from acetonitrile, giving 1.5 g (83%) of colorless crystals, X 105 SC 104 SA 127 I.

Workup

  1. customThe crude product is separated off by column chromatography on silica gel 60 using heptane/ethyl acetate 9:1 (v/v) as eluent
  2. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-3615f63e61c141168aab209d3977a634
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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