Potassium Phosphate, Tribasic → N-(6-Cyclopropyl-pyridin-2-yl)-2,2-dimethyl-propionamide

HRID 531442Notes

Reaction equation

HRID 531442 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=1.[CH:15]1(B(O)O)[CH2:17][CH2:16]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(C)C=CC=CC=1.O>[CH:15]1([C:2]2[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16]1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 9921361N-(6-Bromopyridin-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 60019882N-(6-Cyclopropyl-pyridin-2-yl)-2,2-dimethyl-propionamideYield 235.8%

Reagents, catalysts & solvents 3

HCID 75806TricyclohexylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 22272177Toluene waterSolvent

Procedure

A mixture of N-(6-bromopyridin-2-yl)pivalamide (2 g, 7.77 mmol), cyclopropylboronic acid (935 mg, 10.88 mmol), potassium phosphate (toluene/water (10/3 mL) taken in screw cap tube was purged with argon for 15 minutes and then added palladium(II)acetate (174 mg, 0.77 mmol), tricyclohexylphosphine (435.7 mg, 1.55 mmol) sequentially, purged argon for another 5 min. The resultant mixture was stirred at 100° C. under closed argon atmosphere. Reaction completed in 14 h, reaction mass was cooled to room temperature, extracted into ethyl acetate, (100 ml) organic portion was washed with water, dried over sodium sulfate and concentrated to afford 4 g of the titled compound. LCMS: m/z=219.0 (M+1).

Workup

  1. customcap tube
  2. customwas purged with argon for 15 minutes
  3. customReaction
  4. customreaction mass
  5. extractionextracted into ethyl acetate, (100 ml) organic portion
  6. washwas washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-df770c310e90419dbc01dccaef5b7d06
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…