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Water → 2-Bromo-1-(2,4-Dichlorophenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine-4-one

HRID 1790041
Notes
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Reaction equation

HRID 1790041 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[CH2:16][CH2:15][N:14]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:13](=[O:24])[C:12]=2[C:11]([CH3:25])=[CH:10]1.[Br:26]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:26][C:10]1[N:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:17]2[CH2:16][CH2:15][N:14]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[C:13](=[O:24])[C:12]=2[C:11]=1[CH3:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 179552401-(2,4-Dichlorophenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-4-one

Product 1

HCID 220384662-Bromo-1-(2,4-Dichlorophenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine-4-oneYield 75%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2,4-dichlorophenyl)-3-methyl-5-(1-piperidinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (200 mg, 0.529 mmol, Example 16) at 0° C. in dry DMF was added NBS (N-bromosuccinimide) (99 mg, 0.555 mmol). The reaction mixture was stirred 1 h at 0° C., and then water was added. The resulting solution was extracted several times with Et2O, the combined organic extracts were dried over MgSO4 and evaporated. The residue was dissolved in CH2Cl2 and filtered through a pad of silica gel to give the title material (180 mg, 75% yield) as an orange solid, which was used in Example 19.

Workup

  1. extractionThe resulting solution was extracted several times with Et2O
  2. dry with materialthe combined organic extracts were dried over MgSO4
  3. customevaporated
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. filtrationfiltered through a pad of silica gel

Sources & evidence

ORD record
ord-fc4081945ad94a06b2047b2452355331
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07071207B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes