Sodium Carbonate → HCID 17982734, compound

HRID 2179579Notes

Reaction equation

HRID 2179579 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>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.CN(C=O)C>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[C:10]2[O:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 179826517-Bromobenzofuran-2-carboxylic acid

Product 1

HCID 17982734HCID 17982734, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

5.0 g (20.7 mmol) of 7-bromo-1-benzofuran-2-carboxylic acid (Example 29A) and 3.78 g (24.9 mmol) of 2-methoxyphenylboronic acid are introduced into 50 ml of DMF. Addition of 31.1 ml of 2 M sodium carbonate solution and 1.2 g (1.04 mmol) of Pd(PPh3)4 is followed by heating to 90° C. After 18 h, the solvent is distilled out. The residue is partitioned between 1N hydrochloric acid and ethyl acetate and extracted three times with 200 ml of ethyl acetate each time. The organic phase is dried over sodium sulphate and concentrated in vacuo. The residue is purified by flash chromatography (silica gel, mobile phase: dichloromethane/methanol/acetic acid 100:10:1). Concentration and drying under high vacuum result in 2.97 g (53.2% of theory) of the title compound.

Workup

  1. distillationthe solvent is distilled out
  2. customThe residue is partitioned between 1N hydrochloric acid and ethyl acetate
  3. extractionextracted three times with 200 ml of ethyl acetate each time
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (silica gel, mobile phase: dichloromethane/methanol/acetic acid 100:10:1)
  7. concentrationConcentration
  8. customdrying under high vacuum

Sources & evidence

ORD record
ord-1ebdd01467d84d279a87eb07ebe6d4e6
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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