Formaldehyde → 9-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-2,3,4,9-tetrahydro-2,6-dimethyl-1H-pyrido[3,4-b]indole

HRID 2198296Notes

Reaction equation

HRID 2198296 reaction equation
Cl.[C:2]1(C)C=CC(NN)=CC=1.BrCCC1C=CC(C(F)(F)F)=NC=1.FC(F)(F)C1N=CC(CCN(C2C=CC(C)=CC=2)N)=CC=1.C(OC(OCC)CCCNC)C.[F:57][C:58]([F:82])([F:81])[C:59]1[N:64]=[CH:63][C:62]([CH2:65][CH2:66][N:67]2[C:75]3[C:70](=[CH:71][C:72]([CH3:76])=[CH:73][CH:74]=3)[C:69]([CH2:77][CH2:78][NH:79][CH3:80])=[CH:68]2)=[CH:61][CH:60]=1.C=O.C(O)(C(F)(F)F)=O>C(#N)C.C(N(CC)CC)C>[F:82][C:58]([F:57])([F:81])[C:59]1[N:64]=[CH:63][C:62]([CH2:65][CH2:66][N:67]2[C:75]3[C:70](=[CH:71][C:72]([CH3:76])=[CH:73][CH:74]=3)[C:69]3[CH2:77][CH2:78][N:79]([CH3:2])[CH2:80][C:68]2=3)=[CH:61][CH:60]=1

Participants

10

Reactant 7

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 139945474,4-Diethoxy-N-methylbutan-1-amineHCID 666017985-(2-(1-p-Tolylhydrazinyl)ethyl)-2-(trifluoromethyl)pyridineHCID 668695375-(2-Bromoethyl)-2-(trifluoromethyl)pyridineHCID 669117432-(1-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5-methyl-1H-indol-3-yl)-N-methylethanamine

Product 1

HCID 442421789-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-2,3,4,9-tetrahydro-2,6-dimethyl-1H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

The title compound is prepared by following General Methods 1, 3 and 4 using p-tolylhydrazine hydrochloride, 5-(2-bromoethyl)-2-(trifluoromethyl)pyridine, and triethylamine (General Method 1), 1-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-1-p-tolylhydrazine (Example 2) and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3) and 2-(1-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-5-methyl-1H-indol-3-yl)-N-methylethanamine (Example 11), formaldehyde and TFA in acetonitrile (General Method 4).

Sources & evidence

ORD record
ord-1b589899655a4ef0a1525ec8dfc264ef
Source dataset
uspto-grants-2012_12
Patent number
US08338447B2

Reaction notes

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