Water → 5-{2-[4-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydro-2H-pyridin-1-yl]-ethoxy}-quinoline

HRID 1250169Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2.[NH:15]1[CH2:20][CH:19]=[C:18]([C:21]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1.C(N(CC)CC)C.O>CS(C)=O.[OH-].[Na+]>[NH:23]1[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:29]2[C:21]([C:18]2[CH2:19][CH2:20][N:15]([CH2:2][CH2:3][O:4][C:5]3[CH:14]=[CH:13][CH:12]=[C:11]4[C:6]=3[CH:7]=[CH:8][CH:9]=[N:10]4)[CH2:16][CH:17]=2)=[CH:22]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 5-(2-chloroethoxy)quinoline (0.5 g, 24 mmol), ), 3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine (0.58 g, 29 mmol) and triethylamine (0.67 ml, 48 mmol) in anhydrous dimethylsulfoxide (20 ml) was allowed to stir for 4 hours at 80° C. The mixture was poured into water dilute with sodium hydroxide solution 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 to give a pale yellow solid, which was triturated with ethanol-ethyl ether to afford a pale yellow solid: mp 202-205° C.

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
customto give a pale yellow solid, which
customwas triturated with ethanol-ethyl ether
customto afford a pale yellow solid

Sources & evidence

ORD record: ord-3d1ee6836bba4a1aa8191636d559eb42
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337336B1

Reaction notes

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