Water → 3-{1-[2-(1H-Indol-4-yloxy)-ethyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-1H-pyrrolo[2,3-b]pyridine

HRID 1250168Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH2:12]Cl)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH:14]1[CH2:19][CH:18]=[C:17]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH2:16][CH2:15]1.C(N(CC)CC)C.O>CS(C)=O>[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH2:12][N:14]3[CH2:15][CH:16]=[C:17]([C:20]4[C:28]5[C:23](=[N:24][CH:25]=[CH:26][CH:27]=5)[NH:22][CH:21]=4)[CH2:18][CH2:19]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-(1H-indol-4-yloxy)ethylchloride (0.5 g, 26 mmol), 3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine (0.61 g, 31 mmol) and triethylamine (0.71 ml, 52 mmol) in anhydrous dimethylsulfoxide (20 ml) was allowed to stir for 4 hours at 80° C. The mixture was poured into water and extracted with ethyl acetate (3×100 ml). The organic layer was washed with water (3×100 ml), sodium bicarbonate and dried over anhydrous sodium sulfate, filtered, and the solvent was removed under vacuum. Chromatography (10% methanol-methylene chloride) afforded 0.95 g (97%) of product as a green oil.

Workup

extractionextracted with ethyl acetate (3×100 ml)
washThe organic layer was washed with water (3×100 ml), sodium bicarbonate
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customthe solvent was removed under vacuum

Sources & evidence

ORD record: ord-d112518c0fdd485e82a1d450ddcca1a3
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337336B1

Reaction notes

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