Water → HCID 64211545, compound

HRID 1044795Notes

Reaction equation

HRID 1044795 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([Br:12])=[CH:7][C:6]=1[F:13])=[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])=[C:6]([F:13])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 90871633HCID 90871633, compound

Product 1

HCID 64211545HCID 64211545, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of the crude azide (110 mg, 0.44 mmol) in THF (3 mL) were added polymer-supported Ph3P (3.0 eq.) and water (1.5 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=0.40 min; [M+CH3CN+H]+=263.14.

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-a9400e70112b41c8b819000c5aeb0cdb
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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