Sodium hydride → HCID 57652582, compound

HRID 1930221Notes

Reaction equation

HRID 1930221 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:17][C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][N:24]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[C:25]2=[O:28])=[CH:20][C:19]=1F>CC(N(C)C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][C:18]=2[Br:17])[C:25](=[O:28])[N:24]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)[CH:23]=[CH:22]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 598182577-bromo-6-fluoro-2-(4-methoxybenzyl)isoquinolin-1(2H)-one

Product 1

HCID 57652582HCID 57652582, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

126 mg (0.625 mmol) of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester were dissolved in 2.5 mL of dimethylacteamide and 30 mg (0.75 mmol) of NaH (60% purity) were added at room temperature. After 15 minutes 181 mg (0.5 mmol) of 7-bromo-6-fluoro-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one (313) were added and stirring was continued at room temperature. After 5.5 h the solvent was removed i. vac. After adding saturated sodium bicarbonatesodium bicarbonate solution, the mixture was extracted twice with dichloromethane. The organic layers were dried with MgSO4 and evaporated. After final purification by preparative HPLC, 182 mg of the product could be isolated. Rt=1.93 min (Method C). Detected mass: 543.5/545.5 (M+H+).

Workup

  1. customwas continued at room temperature
  2. customAfter 5.5 h the solvent was removed i
  3. additionAfter adding saturated sodium bicarbonatesodium bicarbonate solution
  4. extractionthe mixture was extracted twice with dichloromethane
  5. dry with materialThe organic layers were dried with MgSO4
  6. customevaporated
  7. customAfter final purification by preparative HPLC, 182 mg of the product
  8. customcould be isolated

Sources & evidence

ORD record
ord-7999c2aaa4714c91aad27fb660bd1dbe
Source dataset
uspto-grants-2012_05
Patent number
US08188117B2

Reaction notes

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