Phenylboronic Acid → HCID 10999447, compound

HRID 2243083Notes

Reaction equation

HRID 2243083 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Ba+2].[OH-]>C1COCC1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl>[C:15]1([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=3)[N:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 6093286Barium hydroxideHCID 109217232-Chloro-6-nitroquinoline

Product 1

HCID 10999447HCID 10999447, compound

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-6-nitroquinoline (10.5 g, 50.4 mmol) (Byoung S. L. et al. Heterocycles. 1998, 48.12, 65), phenylboronic acid (7.4 g, 60.4 mmol), palladium dichloride bis(triphenylphosphine) (0.70 g, 1.01 mmol) and barium hydroxide (38.1 g, 0.121 mol) in 200 ml of anhydrous THF are stirred at 65° C. for 20 hours. The mixture is diluted with water, extracted with CH2Cl2 and evaporated, and the residue is chromatographed on silica gel (1/1 hexane/ethyl acetate). Yield: 7.8 g (62%); IR (KBr): 3475, 3357, 1592, 1479 cm−1.

Workup

  1. extractionextracted with CH2Cl2
  2. customevaporated
  3. customthe residue is chromatographed on silica gel (1/1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-099cc84aef6a4df68330894a3fb2c6e9
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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