Pyridine → HCID 66778275, compound

HRID 406339Notes

Reaction equation

HRID 406339 reaction equation
O[CH2:2][CH2:3][CH:4]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[CH2:5][C:6]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7].N1C=CC=CC=1.C(Br)(Br)(Br)[Br:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:34][CH2:2][CH2:3][CH:4]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[CH2:5][C:6]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7]

Participants

6

Reactant 4

HCID 1049PyridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66778836HCID 66778836, compound

Product 1

HCID 66778275HCID 66778275, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl N′-[5-hydroxy-3-(3-trifluoromethylphenyl)pentanoyl]hydrazinecarboxylate (2.0 g) was dissolved in methylene chloride (53 mL). Pyridine (1.29 mL), carbon tetrabromide (2.64 g) and triphenylphosphine (2.1 g) were added at room temperature, followed by stirring for 30 minutes. The reaction solution was partitioned with water and ethyl acetate. Then, the organic layer was washed with saturated ammonium chloride aqueous solution and a saturated sodium bicarbonate aqueous solution and dried over magnesium sulfate. Concentration under reduced pressure gave an oil. The oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 50%) to obtain the title compound (1.6 g).

Workup

  1. customThe reaction solution was partitioned with water and ethyl acetate
  2. washThen, the organic layer was washed with saturated ammonium chloride aqueous solution
  3. dry with materiala saturated sodium bicarbonate aqueous solution and dried over magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customgave an oil
  6. customThe oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 50%)

Sources & evidence

ORD record
ord-2267ae10186c4ceeb69ad0f94d630d60
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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