Potassium Carbonate → HCID 4189043, compound

HRID 1051532Notes

Reaction equation

HRID 1051532 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1401098-BromoquinolineHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 4189043HCID 4189043, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
120 °C

Procedure

To a solution of 8-bromoquinoline (208.05 mg, 1.0 mmol) in dioxane/H2O (10 mL) was added (3-methoxyphenyl)boronic acid (182.3 mg, 1.2 mmol), Pd(dppf)Cl2 (100 mg) and K2CO3 (276 mg, 2 mmol). The reaction mixture was heated at 120° C. under microwave conditions for 30 minutes before cooling and being concentrated to remove the solvents. The residue was dissolved in ethyl acetate, washed with water and the separated organic layer concentrated to yield a crude product which was used in next step without further purification. (312 mg, Yield 90%). LCMS (m/z): 236.1 (M+1).

Workup

  1. temperaturebefore cooling
  2. concentrationbeing concentrated
  3. customto remove the solvents
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. concentrationthe separated organic layer concentrated

Sources & evidence

ORD record
ord-d68f34c0ee7d429f98744c28731b45ab
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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