1H-Pyrrolo(2,3-b)pyridine → HCID 21110062, compound

HRID 1766156Notes

Reaction equation

[H-].[Na+].[NH:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1.Cl[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1>CN(C)C=O>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[N:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1

Participants

Conditions

Temperature: 20 °C

Procedure

0.894 g of 60% sodium hydride (37.25 mmol) was added with stirring to 20 cm3 of dimethylformamide under an argon atmosphere at a temperature in the region of 20° C. and then a solution of 4 g (33.86 mmol) of 1H-pyrrolo[2,3-b]pyridine in 20 cm3 of dimethylformamide was gradually added. After stirring at a temperature in the region of 20° C. for 30 minutes, a solution of 5.816 g (35.55 mmol) of 2-chloroquinoline in 20 cm3 of dimethylformamide was added and then the reaction mixture was heated at a temperature in the region of 100° C. for 15 h. After concentrating to dryness under reduced pressure (2.7 kpa), the residue was taken up in 150 cm3 of water. The residual oil was taken up in 50 cm3 of diethyl ether. The light yellow crystals that formed were filtered off and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 20° C. 4.39 g of 1-(quinolin-2-yl)-1H-pyrrolo[2,3-b]pyridine were thus obtained in the form of an off-white solid melting at 129° C.

Workup

temperaturethe reaction mixture was heated at a temperature in the region of 100° C. for 15 h
concentrationAfter concentrating to dryness under reduced pressure (2.7 kpa)
customThe light yellow crystals that formed
filtrationwere filtered off
customdried under reduced pressure (2.7 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record: ord-f9a0bb48d65f40fe9274de56b03fd3ce
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230007B2

Reaction notes

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