Triethylamine → 4-bromo-N-{[(1R,2R)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}benzamide

HRID 1639858Notes

Reaction equation

HRID 1639858 reaction equation
Cl.Cl.[CH3:3][N:4]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[C@@H:13]2[CH2:15][C@H:14]2[CH2:16][NH2:17])=[N:5]1.C(N(CC)CC)C.[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>O1CCCC1>[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:17][CH2:16][C@@H:14]2[CH2:15][C@H:13]2[C:10]2[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=2)=[N:5][N:4]([CH3:3])[CH:12]=3)=[O:31])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 667207431-[(1R,2R)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine dihydrochloride

Product 1

HCID 593346434-bromo-N-{[(1R,2R)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}benzamideYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[(1R,2R)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine dihydrochloride (200 mg, 0.729 mmol) and triethylamine (407 μL, 2.92 mmol) in tetrahydrofuran (7 mL) was added 4-bromobenzoyl chloride (192 mg, 0.875 mmol), and the mixture was stirred at room temperature for 1 hr. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→90/10) to give the title compound (247 mg, yield 88%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→90/10)

Sources & evidence

ORD record
ord-43f7e32ca39c463aab539a8e89a60b1b
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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