Triphenylphosphine → HCID 178454104, compound

HRID 707413Notes

Reaction equation

HRID 707413 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([F:12])([F:11])[C:9](=[O:13])[NH:8][C:5]2=[N:6][CH:7]=1.[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:8]2[C:5]3=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=[C:4]3[C:10]([F:12])([F:11])[C:9]2=[O:13])[CH2:24]1)([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 72218242HCID 72218242, compoundHCID 178454125HCID 178454125, compound

Product 1

HCID 178454104HCID 178454104, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

5-Bromo-3,3-difluoro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (1.19 g, 4.78 mmol), tert-butyl(cis-3-hydroxycyclobutyl)carbamate (0.895 g, 4.78 mmol), and triphenylphosphine (1.88 g, 7.17 mmol) were mixed in THF (18 mL) under an argon atmosphere. The mixture was cooled to 0° C. before diisopropyl azodicarboxylate (1.409 mL, 7.17 mmol) was added dropwise via syringe. The reaction mixture was warmed to room temperature and stirred for 19 h. The reaction mixture was diluted with saturated aqueous sodium bicarbonate 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 via silica gel column chromatography eluting with EtOAc in hexanes to yield the title compound (0.477 g, 1.141 mmol, 23.9% 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 via silica gel column chromatography
  9. washeluting with EtOAc in hexanes

Sources & evidence

ORD record
ord-c092c67ac746496fbe8f788c5c0d9ed1
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

Loading…