1H-Pyrrolo(2,3-b)pyridine → HCID 21110056, compound

HRID 1766153Notes

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[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1>CN(C)C=O>[C:13]1([N:3]2[C:7]3=[N:8][CH:9]=[CH:10][CH:11]=[C:6]3[CH:5]=[CH:4]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=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 1-chloroisoquinoline 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 2 times 50 cm3 of water. The residual oil was taken up in 30 cm3 of diethyl ether. The white crystals that formed were filtered off and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 20° C. 4.36 g of 1-(isoquinolin-1-yl)-1H-pyrrolo[2,3-b]pyridine were thus obtained in the form of an off-white solid melting at 87° 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 white 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-8ed82a29e5ec4263b87a7958abc482f9
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230007B2

Reaction notes

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