Sodium Carbonate → HCID 67997048, compound

HRID 470393Notes

Reaction equation

HRID 470393 reaction equation
Cl[C:2]1[C:7]([Br:8])=[CH:6][N:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([C:27]#[N:28])=[CH:19][CH:18]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[Br:8][C:7]1[C:2]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([C:27]#[N:28])=[CH:19][CH:18]=2)=[N:3][CH:4]=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 122700785-Bromo-4-chloropyrimidineHCID 679975564-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthonitrile

Product 1

HCID 67997048HCID 67997048, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-5-bromopyrimidine (193 mg, 1 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthonitrile (279 mg, 1 mmol) palladium tetrakis triphenylphoshine (0.023 g, 0.02 mmol) and aqueous sodium carbonate solution (2M, 1.5 mL, 3 mmol) in dioxane (3 mL) was heated to 80° C. for 12 hours. The reaction mixture cooled to room temperature, washed with water, extracted with ethyl acetate and purified by chromatography to yield 4-(5-bromopyrimidin-4-yl)-1-naphthonitrile (214 mg, 69%).

Workup

  1. temperatureThe reaction mixture cooled to room temperature
  2. washwashed with water
  3. extractionextracted with ethyl acetate
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-6e127a2546f34698816b17c8aadedee5
Source dataset
uspto-grants-2014_01
Patent number
US08629278B2

Reaction notes

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