Furan, 2-(bromomethyl)tetrahydro- → N-Cyclopropyl-3-fluoro-4-methyl-5-[1-(tetrahydro-2-furanylmethyl)-1H-indazol-5-yl]benzamide

HRID 2246630Notes

Reaction equation

HRID 2246630 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[CH2:32][CH2:31][CH2:30][O:29]1>CN(C=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[CH2:32][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

5

Reactant 3

HCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 24758Sodium hydrideHCID 10403067N-Cyclopropyl-3-fluoro-5-(1H-indazol-5-yl)-4-methylbenzamide2×

Product 1

HCID 58899620N-Cyclopropyl-3-fluoro-4-methyl-5-[1-(tetrahydro-2-furanylmethyl)-1H-indazol-5-yl]benzamideYield 29.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure for Example 1 was followed using sodium hydride (60% in mineral oil, 12 mg), N-cyclopropyl-3-fluoro-5-(1H-indazol-5-yl)-4-methylbenzamide (Intermediate 3, 45 mg) and 2-(bromomethyl)tetrahydrofuran (26 mg) in DMF (5 ml) to give the title compound as a colourless glass (17 mg).

Sources & evidence

ORD record
ord-de315485c0c24999b3361602fdb5b8ef
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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