1-Propylboronic acid → HCID 68688475, compound

HRID 1159113Notes

Reaction equation

HRID 1159113 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 atmosphere. 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-beee87bfd33a4f098c9dc4e61cc18522
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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