Water → HCID 71254034, compound

HRID 332112Notes

Reaction equation

HRID 332112 reaction equation
[N:1]([CH2:4][CH:5]([F:22])[CH2:6][N:7]1[C:19]2[CH:18]=[CH:17][C:16]([Br:20])=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[C:11]([Br:21])[CH:12]=2)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[Br:21][C:11]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:6][CH:5]([F:22])[CH2:4][NH2:1])[C:19]3[C:14]([C:13]=2[CH:12]=1)=[CH:15][C:16]([Br:20])=[CH:17][CH:18]=3

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 71254214HCID 71254214, compound

Product 1

HCID 71254034HCID 71254034, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

9-(3-azido-2-fluoropropyl)-3,6-dibromo-9H-carbazole (60 mg, 0.14 mmol) and triphenylphosphine (44 mg, 0.168 mmol) were combined in 0.5 mL of THF and stirred overnight at 60° C. Upon completion 1 ml of H2O was added and the mixture was stirred for 1 hour. The mixture was extracted with EtOAc. The organic layer was washed with H2O, brine, and dried over Na2SO4 and concentrated to a white foam. This material was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionThe mixture was extracted with EtOAc
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a white foam
  6. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-f27e0d06859749f9bd859fe2b74d5b88
Source dataset
uspto-grants-2014_11
Patent number
US08877797B2

Reaction notes

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