HCID 68741658, compound → HCID 59212643, compound

HRID 2244889Notes

Reaction equation

HRID 2244889 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([N:11]1[CH2:16][CH2:15][N:14]([C:17]3([C:30]#N)[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[CH2:13][C@@H:12]1[CH3:32])[CH2:6][CH2:5]2.C[Mg]Br>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([N:11]1[CH2:16][CH2:15][N:14]([C:17]3([CH3:30])[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]3)[CH2:13][C@@H:12]1[CH3:32])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 68741658HCID 68741658, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59212643HCID 59212643, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-[(3S)-4-(5-bromo-2,3-dihydro-1H-inden-1-yl)-3-methylpiperazin-1-yl]-4-cyanopiperidine-1-carboxylate (0.32 g, 0.64 mmol) in THF (2 mL) was added a 3 M solution of methylmagnesium bromide (1.1 mL, 3.3 mmol). After stirring at room temperature overnight, the solution was concentrated. Purification on silica (2:1 hexane/EtOAc) afforded the title compound (0.25 g). MS calculated for C25H37BrN3O2: (M+H)+ 491; found 491.2, 494.2.

Workup

  1. concentrationthe solution was concentrated
  2. customPurification on silica (2:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-f5edfef267964f3792f269a28e7c8359
Source dataset
uspto-grants-2010_03
Patent number
US07678798B2

Reaction notes

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