4-Fluorophenylboronic acid → HCID 18444638, compound

HRID 490385Notes

Reaction equation

HRID 490385 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.I[C:12]1[CH:25]=[CH:24][C:15]([O:16][CH2:17][C:18]2[CH:22]=[CH:21][O:20][C:19]=2[CH3:23])=[CH:14][CH:13]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]3[CH:22]=[CH:21][O:20][C:19]=3[CH3:23])=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 18444641HCID 18444641, compound

Product 1

HCID 18444638HCID 18444638, compound

Conditions

Temperature
95 °C

Procedure

A mixture of (4-fluoro-phenyl)-boronic acid (300 mg, 2.1 mmoles), 3-(4-iodophenoxymethyl)-2-methyl-furan (123). (500 mg, 1.6 mmoles) and potassium acetate (0.6 g) in N,N-dimethylformamide (70 mL) was degassed, treated with [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (90 mg) and the mixture was agitated at 95° C. for 12 hours under an argon atmosphere. The mixture was concentrated in vacuo, partitioned between water (100 ml) and diethyl ether (200 ml). The aqueous phase was re-extracted with diethyl ether, and the combined ethereal phases were dried and evaporated. The residue was purified by flash chromatography, using diethyl ether as eluent, to afford compound 124 (200 mg) as a solid. This material was used directly.

Workup

  1. custom(500 mg, 1.6 mmoles) and potassium acetate (0.6 g) in N,N-dimethylformamide (70 mL) was degassed
  2. additiontreated with [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (90 mg)
  3. concentrationThe mixture was concentrated in vacuo
  4. custompartitioned between water (100 ml) and diethyl ether (200 ml)
  5. extractionThe aqueous phase was re-extracted with diethyl ether
  6. customthe combined ethereal phases were dried
  7. customevaporated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-33bb83027f774a89a832456144bc07e2
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Reaction notes

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