Potassium Carbonate → HCID 23595913, compound

HRID 2426977Notes

Reaction equation

HRID 2426977 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][N:9]=1.[C:15]1(B(O)O)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>O.C(O)C.C1C=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>[C:23]1([C:11]2[CH:12]=[CH:13][C:8]([NH2:7])=[N:9][CH:10]=2)[C:24]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 706222-Amino-5-bromopyridineHCID 2545321-Naphthaleneboronic acid

Product 1

HCID 23595913HCID 23595913, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (5.19 mmol, 717 mg) in water (2.5 mL) and tetrakis(triphenylphosphine)palladium(0) (0.04 mol %, 80 mg) in ethyl alcohol (2.5 mL) were added to 2-amino-5-bromopyridine (1.73 mmol, 299 mg) and 1-naphthaleneboronic acid (2.60 mmol, 446 mg) in benzene (10.0 mL). After 2 hours at 90° C. the reaction mixture was quenched with water (30 mL) and extracted with dichloromethane (3×30 mL). The organic phases were concentrated in vacuo and the residue chromatographed on silica gel (eluted with 50% ethyl acetate in hexanes) to give 260 mg (Y: 68%) of the title compound 11a. MS (E+) m/z: 381 (MH+).

Workup

  1. customAfter 2 hours at 90° C. the reaction mixture was quenched with water (30 mL)
  2. extractionextracted with dichloromethane (3×30 mL)
  3. concentrationThe organic phases were concentrated in vacuo
  4. customthe residue chromatographed on silica gel (eluted with 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-075f07cbb6424f21b1c1385956d01988
Source dataset
uspto-grants-2011_06
Patent number
US07968577B2

Reaction notes

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