Dichloromethane → HCID 59007072, compound

HRID 130403Notes

Reaction equation

HRID 130403 reaction equation
Br[C:2]1[N:7]=[C:6]([S:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[S:18]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19]1.ClCCl>C(=O)([O-])[O-].[Na+].[Na+].CN1CCCC1=O.O>[S:18]1[CH:22]=[CH:21][C:20]([C:2]2[N:7]=[C:6]([S:8]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:10])=[O:9])[CH:5]=[CH:4][CH:3]=2)=[CH:19]1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 581760Thiophene-3-boronic acidHCID 59007102HCID 59007102, compound

Product 1

HCID 59007072HCID 59007072, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 10340Sodium CarbonateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of phenyl 6-bromo-2-pyridinesulfonate (D7) (1.0 g, 7.2 mmol), 3-thienylboronic acid (532 mg, 8 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (80 mg) in sodium carbonate (2M solution, 5 ml) and 1-methyl-2-pyrrolidinone (8 ml) was heated at 130° C. in a microwave reactor for 5 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (1:40 to 1:5 ethyl acetate:hexanes) to afford the title product (D8). MS (ES+) m/e 318 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (1:40 to 1:5 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-8e470ecb1fba4f1aa3851a1d8367dc5d
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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