Sodium hydride → N-Cyclopropyl-3-fluoro-4-methyl-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-indazol-5-yl]benzamide

HRID 2246629Notes

Reaction equation

HRID 2246629 reaction equation
[H-].[Na+].[CH:3]1([NH:6][C:7](=[O:25])[C:8]2[CH:13]=[C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[NH:19][N:18]=[CH:17]4)[C:11]([CH3:23])=[C:10]([F:24])[CH:9]=2)[CH2:5][CH2:4]1.Br[CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1>CN(C=O)C.C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH:3]1([NH:6][C:7](=[O:25])[C:8]2[CH:13]=[C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH2:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[N:18]=[CH:17]4)[C:11]([CH3:23])=[C:10]([F:24])[CH:9]=2)[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 10403067N-Cyclopropyl-3-fluoro-5-(1H-indazol-5-yl)-4-methylbenzamide2×

Product 1

HCID 11292707N-Cyclopropyl-3-fluoro-4-methyl-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-indazol-5-yl]benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584013Chloroform ethylacetateSolvent

Procedure

Sodium hydride (60% in mineral oil, 12 mg) was added to N-cyclopropyl-3-fluoro-5-(1H-indazol-5-yl)-4-methylbenzamide (Intermediate 3, 45 mg) in DMF (5 ml) and the mixture was stirred at room temperature for 1 h. 2-(Bromomethyl)tetrahydro-2H-pyran (20.5 μl) was added and stirring continued for 18 h. The mixture was diluted with chloroform/ethyl acetate (1:1, 5 ml) and washed with water (2×5 ml). The organic phase was concentrated under vacuum and the residue was purified by preparative HPLC to give the title compound as a colourless glass (23 mg).

Workup

  1. stirringstirring
  2. waitcontinued for 18 h
  3. washwashed with water (2×5 ml)
  4. concentrationThe organic phase was concentrated under vacuum
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1229b14028bb485c805ddc8e30b838cf
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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