Trifluoroacetic acid → HCID 21952748, compound

HRID 2215918Notes

Reaction equation

HRID 2215918 reaction equation
C(OC([N:8]1[CH2:22][CH2:21][C:11]2[NH:12][C:13]3[C:14]([C:19]#[N:20])=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:9]1[C:10]2[C:18]3[C:13](=[C:14]([C:19]#[N:20])[CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH2:21][CH2:22][NH:8]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 67182945HCID 67182945, compound

Product 1

HCID 21952748HCID 21952748, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-cyano-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester (1.00 g) in CH2Cl2 (10 mL) was treated with TFA (2 mL). The reaction mixture was stirred for 7 h then converted to the free base with K2CO3 to provide 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-6-carbonitrile (0.66 g, 99%) as a white solid: mp 230–235° C.; 1H NMR (300 MHz, CD3OD) δ 7.71–7.69 (m, 1H), 7.50–7.46 (m, 1H), 7.16–7.11 (m, 1H), 4.05–4.04 (m, 2H), 3.26–3.21 (m, 2H), 2.91–2.87 (m, 2H); ESI MS m/z 198 [C12H, N3+H]+.

Sources & evidence

ORD record
ord-b098e9a0a5004ca6bc8f4b5638bb7ffc
Source dataset
uspto-grants-2006_09
Patent number
US07109339B2

Reaction notes

Loading…