Triphenylphosphine → HCID 178454105, compound

HRID 707406Notes

Reaction equation

HRID 707406 reaction equation
[F:1][C:2]1([F:13])[C:10]2[C:5](=[N:6][CH:7]=[C:8]([F:11])[CH:9]=2)[NH:4][C:3]1=[O:12].[C:14]([O:18][C:19](=[O:26])[NH:20][C@H:21]1[CH2:24][C@@H:23](O)[CH2:22]1)([CH3:17])([CH3:16])[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C([O-])(O)=O.[Na+]>[C:14]([O:18][C:19](=[O:26])[NH:20][C@H:21]1[CH2:22][C@H:23]([N:4]2[C:5]3=[N:6][CH:7]=[C:8]([F:11])[CH:9]=[C:10]3[C:2]([F:1])([F:13])[C:3]2=[O:12])[CH2:24]1)([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 847191103,3,5-Trifluoro-1H,2H,3H-pyrrolo[2,3-b]pyridin-2-oneHCID 178454125HCID 178454125, compound

Product 1

HCID 178454105HCID 178454105, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3,3,5-Trifluoro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (0.248 g, 1.318 mmol), tert-butyl(cis-3-hydroxycyclobutyl)carbamate (0.247 g, 1.318 mmol), and triphenylphosphine (0.519 g, 1.978 mmol) were mixed in THF (5 mL) under an argon atmosphere. The mixture was cooled to 0° C. before diisopropyl azodicarboxylate (0.389 mL, 1.978 mmol) was added dropwise via syringe. The reaction mixture was warmed to room temperature and stirred for 22 h. The reaction mixture was diluted with sat. NaHCO3 and extracted with EtOAc. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography eluting with EtOAc in hexanes to yield the title compound (0.241 g, 0.674 mmol, 51.2% yield) as a white solid.

Workup

  1. additionwas added dropwise via syringe
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude product was purified by silica gel column chromatography
  9. washeluting with EtOAc in hexanes

Sources & evidence

ORD record
ord-4530ecf4004f4e5abe83dad157ec323f
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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