Nanofin → HCID 59305341, compound

HRID 2240994Notes

Reaction equation

HRID 2240994 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9](=[O:22])[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([F:21])[F:20])=[CH:14][CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].C[CH:24]1[CH2:29][CH2:28][CH2:27][CH:26](C)N1.C(C1CC1)#C>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH:28]1([C:27]#[C:26][C:2]2[CH:3]=[C:4]([C:9](=[O:22])[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:19]([F:21])[F:20])=[CH:14][CH:13]=3)=[O:11])[CH:5]=[CH:6][C:7]=2[F:8])[CH2:29][CH2:24]1

Participants

6

Reactant 3

HCID 68843NanofinHCID 138823CyclopropylacetyleneHCID 59790308HCID 59790308, compound

Product 1

HCID 59305341HCID 59305341, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(3-bromo-4-fluorophenyl)-2-[4-(difluoromethoxy)phenyl]ethane-1,2-dione (2.1 g, 5.63 mmol), 2,6-dimethylpiperidine (10 mL), and ethynylcyclopropane (0.74 g, 11.27 mmol) was degassed with argon for 5 minutes. Then, tetrakis(triphenylphosphine) palladium (0) (327 mg, 0.28 mmol) was added and the mixture was stirred at 80° C. for 5 hours. The mixture was poured into water and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by ICSO (hexane/EtOAc 5/1) gave 1-[3-(cyclopropylethynyl)-4-fluorophenyl]-2-[4-(difluoromethoxy)phenyl]ethane-1,2-dione as a yellow oil solid (1.37 g); MS m/e (M)+ 358.

Workup

  1. customwas degassed with argon for 5 minutes
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and purification by ICSO (hexane/EtOAc 5/1)

Sources & evidence

ORD record
ord-a79d1c5abf5a447cb9ed4bf89754b2f5
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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