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

HRID 1940540Notes

Reaction equation

HRID 1940540 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)=[CH:5][CH:4]=1.CN([CH2:18][C:19]1[C:27]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)C>CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH2:14][CH2:13][N:12]([CH2:18][C:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH2:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 53835493-(Dimethylaminomethyl)-7-azaindoleHCID 135448404-(4-Methoxyphenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 214629763-(4-[4-Methoxyphenyl]-1,2,3,6-tetrahydropyridin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridineYield 41%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-(4-Methoxyphenyl)-1,2,3,6-tetrahydropyridine (540 mg, 2.8 mmol) was reacted with 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.8 mmol) as in Example 4 to give the title compound (367 mg, 41%) as tan crystals, m.p. 202°-204° C. (iPrOH); (Found: C, 73.51; H, 6.74; N, 12.15. C20H21N3O.0.33 H2O.0.2 C3 H8O requires C, 73.34; H, 6.95; N, 12.45%); δH (DMSO-d6) 2.44 (2H, m, tetrahydropyridinyl CH2), 2.70 (2H, m, tetrahydropyridinyl CH2), 3.10 (2H, m, tetrahydropyridinyl CH2), 3.74 (3H, s, ArOCH3), 3.76 (2H, s, ArCH2N), 6.04 (1H, m, CH=CR), 6.90 (2H, d, J 8.6 Hz, ArH), 7.04 (1H, dd, J 7.7, 4.6 Hz, 5-H), 7.36 (2H, d, J 8.5 Hz, ArH), 7.40 (1H, s, 2-H), 8.06 (1H, d, J 7.7 Hz, 4-H), 8.20 (1H, d, J 4.6 Hz, 6-H), and 11.48 (1H, br s, NH); m/z (CI+, NH3) 320 (M+1)+.

Sources & evidence

ORD record
ord-280d9118d90a451aacda53f9d31c87e3
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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