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

HRID 54218Notes

Reaction equation

HRID 54218 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CN([CH2:19][C:20]1[C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)C>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[N:10]1[CH2:15][CH2:14][N:13]([CH2:19][C:20]2[C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 53835493-(Dimethylaminomethyl)-7-azaindoleHCID 190649741-(Benzothiophen-2-yl)piperazine

Product 1

HCID 199585103-(4-(Benzothiophen-2-yl)piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridineYield 54%

Procedure

The title compound was prepared in an analogous manner to Example 6, Step 3 using 1-(benzothiophen-2-yl)piperazine (180 mg, 0.83 mmol) and 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (145 mg, 0.83 mmol). Recrystallisation from ethyl acetatehexane afforded the title compound (155 mg, 54%), m.p. 269° C. (dec.); (Found: C, 69.10; H, 5.85; N, 16.08. C20H20N4S requires C, 68.94; H, 5.79; N, 16.08%); δH (DMSO-d6) 2.55 (4H, t, J 5 Hz, 2×piperazinyl CH2), 3.18 (4H, t, J 5 Hz, 2×piperazinyl CH2), 3.70 (2H, s, indole-CH2N), 6.26 (1H, s, 3-H-benzothiophene), 7.04 (2H, m, 2×ArH), 7.19 (1H, m, ArH), 7.05 (2H, m, 2×ArH), 7.63 (1H, d, 8 Hz, ArH), 8.06 (1H, d, 8 Hz, ArH), 8.20 (1H, d, 3 Hz, ArH), and 11.46 (1H, br s, NH); m/z (CI+, NH3) 349 (M+1)+.

Workup

  1. customRecrystallisation from ethyl acetatehexane

Sources & evidence

ORD record
ord-ea1fc869749a498198ce6750acdd2924
Source dataset
uspto-grants-1997_04
Patent number
US05622950

Reaction notes

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