3-(Dimethylaminomethyl)-7-azaindole → HCID 19614004, compound

HRID 1600479Notes

Reaction equation

HRID 1600479 reaction equation
[I: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>[I: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 177501621-(5-Iodopyridin-2-yl)piperazine

Product 1

HCID 19614004HCID 19614004, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(5-iodopyridin-2-yl)-piperazine (100 mg, 0.34 mmol) in toluene (2 mL) (prepared in Example 2(b)) was added 3-(N,N-dimethylaminomethyl)-1H-pyrrolo[2,3-b]pyridine (58 mg, 0.32 mmol) (prepared in Example 1(a)). The mixture was heated at reflux over night and then allowed to cool to room temperature. The resulting solid was filtered and dried in vacuo to give 3-[4-(5-iodopyridin-2-yl)-piperazin-1-yl]methyl-1H-pyrrolo[2,3-b]pyridine as a colourless solid (118 mg, 79%). δH(300 MHz DMSO-d6) 2.47 (4H, m, piperazinyl), 3.45 (4H, m, piperazinyl), 3.68 (2H, s), 6.71 (1H, d, J=9), 7.05 (1H, dd, J=4.8 and 7.9), 7.39 (1H, s), 7.75 (1H, d, J=8.8), 8.06 (1H, d, J=7.8), 8.21 (1H, d, J=4.5), 8.23 (1H, s), 11.51 (1H, br s, NH)

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux over night
  3. filtrationThe resulting solid was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ab30386463164eb1bea6244af6836028
Source dataset
uspto-grants-1999_11
Patent number
US05976497

Reaction notes

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