3-(Dimethylaminomethyl)-7-azaindole → HCID 18942174, compound

HRID 355394Notes

Reaction equation

HRID 355394 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[CH3:3].[F:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]2[CH2:24]CNC[CH:28]=2)=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[F:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]2[CH2:24][CH2:3][N:2]([CH2:4][C:5]3[C:13]4[C:8](=[N:9][CH:10]=[CH:11][CH:12]=4)[NH:7][CH:6]=3)[CH2:1][CH:28]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 53835493-(Dimethylaminomethyl)-7-azaindoleHCID 18942183HCID 18942183, compound

Product 1

HCID 18942174HCID 18942174, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-dimethylaminomethyl- 1H-pyrrolo[2,3-b]pyridine (1.57 g, 9 mmol) and (E)-4-[2-(4-fluorophenyl)ethenyl]-1,2,3,6-tetrahydropyridine (2 g, 9 mmol) in toluene (50 ml) was refluxed overnight. The hot solution was filtered, and the product crystallised from toluene to give (E)-3-[4-[2-(4-fluorophenyl)ethenyl]-1,2,3,6-tetrahydropyridin-1-yl]methylpyrrolo[2,3-b]pyridine (1.2 g, 40%). M.p. 211°-213° C. (isopropanol). (Found: C, 75.05; H, 5.99; N,12.27; C21H20 FN3, 0.15H2O requires C, 75.04; H, 6.09; N, 12.50%); δH (DMSO-d6) 2.29 (2H, br s, tetrahydropyridinyl CH2), 2.61 (2H, t, J 5.6 Hz tetrahydropryridinyl CH2), 3.06 (2H, br s, tetrahydropyridinyl CH2), 3.73 (2H, s, NCH2Ar), 5.87 (1H, br s, tetrahydropyridinyl 5-CH), 6.45 (1H, d, J 16.3 Hz, ArCHCHC), 6.83 (1H, d, J 16.3 Hz, ArCHCHC), 7.01-7.04 (1H, m, ArH), 7.14 (2H, t, J 8.9 Hz, ArH), 7.38 (1H, s, ArH), 7.47-7.51 (2H, m, ArH), 8.02 (1H, d, J 7.9 Hz, ArH), 8.18-8.20 (1H, m, ArH) and 11.45 (1H, br s, NH); m/z (CI+, NH3), 334 (M+1)+.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe hot solution was filtered
  3. customthe product crystallised from toluene

Sources & evidence

ORD record
ord-7f18e728bb564cdcaf28f0bd56c4f4b9
Source dataset
uspto-grants-1998_11
Patent number
US05830901

Reaction notes

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