Sodium Carbonate → HCID 66748903, compound

HRID 1405937Notes

Reaction equation

HRID 1405937 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][C:16]=1[F:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[C:26]1[C:27]([NH2:32])=[N:28][CH:29]=[CH:30][CH:31]=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>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:26]2[C:27]([NH2:32])=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:17][C:16]=1[F:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 8177002-Amino-3-bromopyridineHCID 27377884-Benzyloxy-3-fluorophenylboronic Acid

Product 1

HCID 66748903HCID 66748903, compoundYield 100%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

A mixture of sodium carbonate (7.18 g), tetrakis(triphenylphosphine)palladium(0) (1.957 g), 4-(benzyloxy)-3-fluorophenylboronic acid (10 g), and 3-bromopyridin-2-amine (5.86 g) in DME (120 mL) and water (24 mL) was stirred at 80° C. overnight. The mixture was added with silica gel, concentrated in vacuo, and purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (9.97 g) as a pale yellow solid.

Workup

  1. additionThe mixture was added with silica gel
  2. concentrationconcentrated in vacuo
  3. custompurified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-bd2affa0991841ae87b6f84ced4f1aa9
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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