P,P-Diphenylphosphinic azide → HCID 67976219, compound

HRID 706583Notes

Reaction equation

HRID 706583 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([CH2:10][N:11]3[C:19]4[CH:18]=[CH:17][C:16]([F:20])=[C:15](C(O)=O)[C:14]=4[C:13]([CH3:24])=[N:12]3)[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C1(P([N:39]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C=O)C.O>[CH:1]1([C:4]2[N:9]=[C:8]([CH2:10][N:11]3[C:19]4[CH:18]=[CH:17][C:16]([F:20])=[C:15]([NH2:39])[C:14]=4[C:13]([CH3:24])=[N:12]3)[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 199401P,P-Diphenylphosphinic azideHCID 67974579HCID 67974579, compound

Product 1

HCID 67976219HCID 67976219, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

1-((6-Cyclopropylpyridin-2-yl)methyl)-5-fluoro-3-methyl-1H-indazole-4-carboxylic acid (0.205 g, 0.630 mmol) was dissolved in 6 mL of DMF. To this was added diphenylphosphoryl azide (0.260 g, 0.945 mmol) and TEA (0.263 mL, 1.89 mmol) and the mixture was stirred at ambient temperature for 1.5 hours. Water (5 mL) was added and the mixture was warmed to 80° C. for 2 hours, then allowed to stir at ambient temperature for 16 hours. The reaction mixture was diluted with water and extracted twice with EtOAc. The combined organic extracts washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography (1:1 EtOAc:Hexanes) of the crude material afforded 0.107 g (57%) of the title compound.

Workup

  1. temperaturethe mixture was warmed to 80° C. for 2 hours
  2. stirringto stir at ambient temperature for 16 hours
  3. extractionextracted twice with EtOAc
  4. washThe combined organic extracts washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-abb53ffd738a4d2f8bd66d047da5d367
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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