3-(Dimethylaminomethyl)-7-azaindole → HCID 19614007, compound

HRID 1600481Notes

Reaction equation

HRID 1600481 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.CN([CH2:17][C:18]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH2:17][C:18]3[C:26]4[C:21](=[N:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 53835493-(Dimethylaminomethyl)-7-azaindoleHCID 164142271-(5-Bromopyridin-2-yl)piperazine

Product 1

HCID 19614007HCID 19614007, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(5-bromopyridin-2-yl)-piperazine (310 mg,1.28 mmol) (prepared in Example 3(b)) and 3-(N,N-dimethylaminomethyl)-1H-pyrrolo[2,3-b]pyridine (215 mg, 1.16 mmol) (prepared in Example 1(a)) in toluene (10 mL) was heated at reflux for 18 h. The heating was discontinued and the solution allowed to cool to room temperature during which time a colourless solid precipitated out of solution. The solid was collected by filtration and dried in vacuo to yield 3-[4-(5-bromopyridin-2-yl)-piperazin-1-yl]methyl-1H-pyrrolo[2,3-b]pyridine as a colourless solid (420 mg, 97%). δH (300 mhz CDCl3) 2.58 (4H, m, piperazinyl), 3.51 (4H, m, piperazinyl), 3.75 (2H, s), 6.50 (1H, d, J=9.0), 7.09 (1H, dd, J=5.0 and 7.9), 7.27 (1H, s), 7.49 (1H, dd, J=2.6 and 9.0), 8.10 (1H, d, J=7.8), 8.17 (1H, d, J=2.3), 8.32 (4.5), 9.69 (1H , br s) ESMS 374 (MH+)

Workup

  1. temperatureat reflux for 18 h
  2. customprecipitated out of solution
  3. filtrationThe solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d7c35d4bc4eb4ea6bb7ac196aecb1d8a
Source dataset
uspto-grants-1999_11
Patent number
US05976497

Reaction notes

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