3-(Dimethylaminomethyl)-7-azaindole → 3-(4-[2-(Furan-2-yl)ethyl]-1,2,3,6-tetrahydropyridin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1940555Notes

Reaction equation

HRID 1940555 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=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>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]1[CH2:9][CH2:10][N:11]([CH2:17][C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[CH2:12][CH:13]=1

Participants

4

Reactant 2

HCID 53835493-(Dimethylaminomethyl)-7-azaindoleHCID 214629694-(2-Furan-2-ylethyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 214629873-(4-[2-(Furan-2-yl)ethyl]-1,2,3,6-tetrahydropyridin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridineYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-(2-[furan-2-yl]ethyl)-1,2,3,6-tetrahydropyridine (506 mg, 2.86 mmol) and 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.86 mmol) in toluene (10 ml) was stirred at reflux for 10 hours. The solvent was evaporated and the residue chromatographed with 3% methanol in dichloromethane as eluant to afford the title compound (200 mg, 23%) as a colourless solid, m.p. 105° C.; (Found: C, 73.84; H, 6.72; N, 13.31. C19H21N3O requires C, 74.24; H, 6.89; N, 13.67); δH (DMSO-d6) 2.00-2.06 (2H, m, tetrahydropyridinyl CH2), 2.22 (2H, t, J 7.7 Hz, CH2), 2.48-2.54 (2H, m, CH2), 2.68 (2H, t, J 7.3 Hz, tetrahydropyridinyl CH2), 2.84-2.89 (2H, m, tetrahydropyridinyl CH2), 3.66 (2H, s, NCH2Ar), 5.34-5.38 (1H, m, tetrahydropyridinyl 5-H), 6.06 (1H, d, J 2.9 Hz, furanyl 3-H), 6.31 (1H, dd, J 3.0, 1.9 Hz, furanyl 4-H), 7.02 (1H, dd, J 7.8, 4.6 Hz, 5-H), 7.32 (1H, d, J 2.3 Hz, furanyl 5-H), 7.46 (1H, d, J 3.0 Hz, 2-H), 7.99 (1H, m, dd, J 7.8, 4.1 Hz, 4-H), 8.18 (1H, dd, J 4.6, 1.4 Hz, 6-H), and 11.38 (1H, br s, NH); m/z (CI+, NH3) 308 (M+1)+.

Workup

  1. temperatureat reflux for 10 hours
  2. customThe solvent was evaporated
  3. customthe residue chromatographed with 3% methanol in dichloromethane as eluant

Sources & evidence

ORD record
ord-a4f281c601e64448af5c0b68a13bc6d7
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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