Potassium Carbonate → HCID 86729194, compound

HRID 868822Notes

Reaction equation

HRID 868822 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:13]=[CH:12][C:11](B3OC(C)(C)C(C)(C)O3)=[CH:10][C:7]=2[C:8]#[N:9])[CH2:3][CH2:2]1.Br[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([Cl:30])[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[Cl:30][C:26]1[CH:25]=[C:24]([C:11]2[CH:12]=[CH:13][C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)=[C:7]([CH:10]=2)[C:8]#[N:9])[CH:29]=[CH:28][N:27]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 38477704-Bromo-2-chloropyridineHCID 71295118HCID 71295118, compound

Product 1

HCID 86729194HCID 86729194, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-cyclopropylmethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (3.0 g, 0.010 mol) in acetonitrile (60 ml) and water (20 ml) is degassed for 10 min. 4-Bromo-2-chloropyridine (1.92 g, 0.010 mol), potassium carbonate (2.76 g, 0.02 mol) and tetrakis(triphenyl phosphine)palladium(0) (0.11 g, 0.0001 mol) are added. The reaction mixture is stirred at 90° C. for 6 h. The mixture is cooled to room temperature, filtered and evaporated in a rotary evaporator. The residue is taken up in ethyl acetate (200 ml), washed with water (2×200 ml) and saturated sodium chloride solution (1×200 ml). The mixture is subsequently dried over sodium sulfate, evaporated in a rotary evaporator and chromatographed for purification, giving 2.1 g of a pale-yellow solid;

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationfiltered
  3. customevaporated in a rotary evaporator
  4. washwashed with water (2×200 ml) and saturated sodium chloride solution (1×200 ml)
  5. dry with materialThe mixture is subsequently dried over sodium sulfate
  6. customevaporated in a rotary evaporator
  7. customchromatographed for purification

Sources & evidence

ORD record
ord-f2f5a1dbe6394dddbf1cc618c026fe29
Source dataset
uspto-grants-2015_03
Patent number
US08969335B2

Reaction notes

Loading…