1-Propylboronic acid → HCID 68688475, compound

HRID 1296321Notes

Reaction equation

HRID 1296321 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[N:7]3[CH2:13][CH2:14][NH:15][CH2:16][C@H:6]3[CH2:5][C:4]=2[CH:3]=1.[CH2:17](B(O)O)[CH2:18][CH3:19].[F-].[K+]>O1CCOCC1.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH2:19]([N:15]1[CH2:14][CH2:13][N:7]2[C:8](=[O:12])[C:9]3[CH:10]=[CH:11][C:2]([CH2:5][CH2:6][CH3:16])=[CH:3][C:4]=3[CH2:5][C@@H:6]2[CH2:16]1)[C:18]1[CH:17]=[CH:4][CH:3]=[CH:2][CH:11]=1

Participants

6

Reactant 3

HCID 3510651-Propylboronic acidHCID 522689Potassium FluorideHCID 58911604HCID 58911604, compound

Product 1

HCID 68688475HCID 68688475, compound

Reagents, catalysts & solvents 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (R)-9-chloro-1,2,3,4,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-6-one (50 mg, 0.15 mmol), bis(tri-t-butyl phosphine) palladium (2.3 mg, 0.0045 mmol), propyl boronic acid (16 mg, 0.18 mmol), and potassium fluoride(19 mg, 0.33 mmol) in anhydrous 1,4-dioxane (2 mL) was degassed, heated to 100° C. and stirred for 6 h under nitrogen atomsphare. Then the mixture was cooled down to room temperature, diluted with 10 ml of EtOAc and filtered through celite pad. The filtrate was concentrated to give the desired product which was used for next step without further purification. MS (ESI) 335 (M+H).

Workup

  1. customwas degassed
  2. temperatureThen the mixture was cooled down to room temperature
  3. additiondiluted with 10 ml of EtOAc
  4. filtrationfiltered through celite pad
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6b830940b8da4a19bc38cc9cf580959b
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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