Sodium hydride → HCID 89600115, compound

HRID 2277701Notes

Reaction equation

HRID 2277701 reaction equation
[H-].[Na+].[N:3]1[NH:4][N:5]=[CH:6][CH:7]=1.Br[CH:9]([C:11]1[CH:12]=[C:13]([N:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:27])[CH:23]=3)[C:18]2=[O:28])[CH:14]=[N:15][CH:16]=1)[CH3:10]>CN(C=O)C>[Cl:27][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:28])[N:17]([C:13]1[CH:14]=[N:15][CH:16]=[C:11]([CH:9]([N:4]3[N:5]=[CH:6][CH:7]=[N:3]3)[CH3:10])[CH:12]=1)[CH2:26][CH2:25]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 675161H-1,2,3-TriazoleHCID 86685994HCID 86685994, compound

Product 1

HCID 89600115HCID 89600115, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (30 mg, 0.12 mmol) was added to a solution of 2H-[1,2,3]triazole (8.3 mg, 0.12 mmol) in DMF (5 mL) at 0° C. and the resulting reaction mixture was stirred for 10 min before 2-[5-(1-bromo-ethyl)-pyridin-3-yl]-6-chloro-3,4-dihydro-2H-isoquinolin-1-one (36.5 mg, 0.1 mmol) was added. After additional stirring at RT for 1 hour, it was poured into ice-water (5 mL) and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was then purified by prep-HPLC to give title compound (7.5 mg, 21%) as a white solid. MS: 354.2 (M+H+).

Workup

  1. customthe resulting reaction mixture
  2. additionwas added
  3. extractionextracted with EtOAc (2×10 mL)
  4. washThe organic layers were washed with brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo
  8. customto give a crude product which
  9. customwas then purified by prep-HPLC

Sources & evidence

ORD record
ord-213d9ebc75e94a7eb61c8156ea4e3cbe
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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