Sodium hydride → HCID 86685983, compound

HRID 2277687Notes

Reaction equation

HRID 2277687 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9]([C:15]1[CH:16]=[N:17][CH:18]=[C:19]([OH:21])[CH:20]=1)[CH2:8][CH2:7]2.[C:22]([O:26][C:27](=[O:30])[CH2:28]Br)([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C>[C:22]([O:26][C:27](=[O:30])[CH2:28][O:21][C:19]1[CH:18]=[N:17][CH:16]=[C:15]([N:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][CH:13]=[C:4]([Cl:3])[CH:5]=3)[C:10]2=[O:14])[CH:20]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 86685981HCID 86685981, compound

Product 1

HCID 86685983HCID 86685983, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (38 mg, 1.5 mmol) was added to a solution of 6-chloro-2-(5-hydroxy-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (288 mg, 1.0 mmol, example 252) in dry DMF (5 mL) at 0° C. After stirred at RT for 10 minutes, bromo-acetic acid tert-butyl ester (234 mg, 1.2 mmol) was added and the reaction mixture was stirred at RT for 1 hour before it was poured into ice-water and extracted with EtOAc (2×10 mL). The combined organic layers were dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (320 mg, 82%) as a solid MS: 389.8 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred at RT for 1 hour before it
  2. extractionextracted with EtOAc (2×10 mL)
  3. customThe combined organic layers were dried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84bb1156b57742ae8588adb0d8b0f635
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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