Diisopropylamine → 2-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamide

HRID 254693

Reaction equation

HRID 254693 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:25])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[N:21][O:22][C:23]=3[CH3:24])=[CH:15][CH:14]=2)[CH3:9])=[N:6][CH:7]=1.[CH:26](B1OC(C)(C)C(C)(C)O1)=[CH2:27].CC1C(P(C2C(C)=CC(C)=C(S([O-])(=O)=O)C=2)C2C(C)=CC(C)=C(S([O-])(=O)=O)C=2)=CC(S([O-])(=O)=O)=C(C)C=1.[Na+].[Na+].[Na+].C(NC(C)C)(C)C>CC#N.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][C:23]1[O:22][N:21]=[CH:20][C:19]=1[C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C:11]([NH:10][C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([CH:26]=[CH2:27])=[CH:7][N:6]=2)[CH3:9])=[O:25])=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 11239198TxptsHCID 24765670N-[(1R)-1-(5-bromopyridin-2-yl)ethyl]-2-[4-(5-methylisoxazol-4-yl)phenyl]acetamide

Product 1

HCID 247655772-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamide

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.18 g (0.46 mmol) N-[(1R)-1-(5-bromopyridin-2-yl)ethyl]-2-[4-(5-methylisoxazol-4-yl)phenyl]acetamide in 0.50 ml CH3CN and 0.50 ml water was added 0.07 g (0.46 mmol) 2-vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.02 g (0.03 mmol) TXPTS, 0.003 g (0.01 mmol) Palladium (II) acetate, and 0.13 mL (0.92 mmol) diisopropylamine. After 20 min in the microwave at 120° C., the reaction mixture was cooled, extracted with CH2Cl2, and washed with brine. The organic layer was dried over NaSO4, filtered, and concentrated in vacuo. Purification by flash chromatography (1×14 cm silica gel, linear gradient 40-85% EtOAc:hexane) afforded 2-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamide. Electrospray mass spec M+H=348.1.

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over NaSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (1×14 cm silica gel, linear gradient 40-85% EtOAc:hexane)

Sources & evidence

ORD record
ord-9e45eab71622477bab1167d7322fd753
Source dataset
uspto-grants-2011_01
Patent number
US07875636B2

Linked notes

Loading…