Water → HCID 66820024, compound

HRID 1044792Notes

Reaction equation

HRID 1044792 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([Br:12])=[C:7]([F:13])[CH:6]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[Br:12][C:8]1[C:9]([F:11])=[CH:10][C:5]([CH2:4][NH2:1])=[CH:6][C:7]=1[F:13]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 90788763HCID 90788763, compound

Product 1

HCID 66820024HCID 66820024, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of the crude azide (70 mg, 0.28 mmol) in THF (4 mL) were added polymer-supported Ph3P (3.0 eq.) and water (1 mL). The reaction mixture was stirred at 55° C. until completion of the reaction, cooled down to rt and filtered. The filtrate was partitioned between EA and aq. sat. NaHCO3 and the layers separated. The aq. layer was extracted with EA and the combined org. extracts dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 07: tR=0.37 min; [M+CH3CN+H]+=263.15.

Workup

  1. temperaturecooled down to rt
  2. filtrationfiltered
  3. customThe filtrate was partitioned between EA and aq. sat. NaHCO3
  4. customthe layers separated
  5. extractionThe aq. layer was extracted with EA
  6. dry with materialextracts dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-65641d00fcbf481b9ad9578fc64fb67b
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

Loading…