Potassium Carbonate → HCID 68465364, compound

HRID 501176Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[N:6][CH:5]=1.[CH2:12]1[C:17]2[NH:18][C:19]3[C:24]([C:16]=2[CH2:15][CH2:14][NH:13]1)=[CH:23][CH:22]=[CH:21][CH:20]=3.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH2:12]1[C:17]2[NH:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]=2[CH2:15][CH2:14][N:13]1[C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:11])=[CH:5][N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl-6-chloronicotinate (170 mg), 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (170 mg), potassium carbonate (150 mg) and dioxane (6 mL) was heated in a 100° C. oil bath overnight. Another aliquote of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (170 mg) was added and the heating was continue for five hours. The reaction was cooled and partitioned between water and EtOAc. The organics were washed with water, dried, and the solvent evaporated. The residue was purified by filtration through silica gel eluting with EtOAc to give methyl 6-(1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)nicotinate as a brown solid (75 mg), m/e=308 (M+1).

Workup

temperatureThe reaction was cooled
custompartitioned between water and EtOAc
washThe organics were washed with water
customdried
customthe solvent evaporated
filtrationThe residue was purified by filtration through silica gel eluting with EtOAc

Sources & evidence

ORD record: ord-e40b2c5d20dd461a9df9ecd20adfc17b
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772245B2

Reaction notes

Loading…