Dichloromethane → HCID 66876703, compound

HRID 2194948Notes

Reaction equation

HRID 2194948 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[N:13]=[CH:12]3)=[CH:7][C:6]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:5](OS(C(F)(F)F)(=O)=O)[CH:4]=1.[CH3:33]B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>CN(C=O)C.C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[N:13]=[CH:12]3)=[CH:7][C:6]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:5]([CH3:33])[CH:4]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 139377Methylboronic AcidHCID 86640867HCID 86640867, compound

Product 1

HCID 66876703HCID 66876703, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Intermediate 4 (23 mg) in DMF (1.0 ml) was added with methyl boronic acid (18 mg, Ald), sodium carbonate (30 mg), and PdCl2dppf.CH2Cl2 (8.0 mg, Ald), and stirred at 120° C. for 8 hours. The reaction mixture was added with water (30 ml), and ethyl acetate (30 ml×2) for extraction, and then successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine, the organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1), and the solvent was evaporated under reduced pressure by using a rotary evaporator to obtain the title compound (yield: 15 mg).

Workup

  1. washsuccessively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
  2. customthe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1)
  5. customthe solvent was evaporated under reduced pressure
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-a038f3e68df74f79b88381a4563cc584
Source dataset
uspto-grants-2012_12
Patent number
US08334314B2

Reaction notes

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