Sodium Carbonate → HCID 66824153, compound

HRID 1405718Notes

Reaction equation

HRID 1405718 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH:7]1([O:13][C:14]2[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Br[C:24]1[C:25]([NH2:31])=[N:26][CH:27]=[C:28]([Cl:30])[CH:29]=1>COCCOC.O.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>[Cl:30][C:28]1[CH:29]=[C:24]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)=[CH:15][CH:16]=2)[C:25]([NH2:31])=[N:26][CH:27]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27639713-Bromo-5-chloropyridin-2-amineHCID 222898184-Cyclohexyloxy-benzeneboronic acid

Product 1

HCID 66824153HCID 66824153, compoundYield 48.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of sodium carbonate (307 mg), tetrakis(triphenylphosphine)palladium(0) (50.1 mg), 4-(cyclohexyloxy)phenylboronic acid (414 mg) and 3-bromo-5-chloropyridin-2-amine (300 mg) in DME (15 mL) and water (3 mL) was stirred at 80° C. for 5 hr. Silica gel was added and the mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (212 mg) as a yellow gum.

Workup

  1. additionSilica gel was added
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-43116dc29ddb4f8e8547ed0096dba6c8
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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