Formaldehyde → 6-chloro-9-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-2,3,4,9-tetrahydro-2-methyl-1H-pyrido[3,4-b]indole
Reaction equation
Cl.Cl[C:3]1C=CC(NN)=CC=1.BrCCC1C=CC(C(F)(F)F)=NC=1.ClC1C=CC(N(CCC2C=NC(C(F)(F)F)=CC=2)N)=CC=1.C(OC(OCC)CCCNC)C.[Cl:57][C:58]1[CH:59]=[C:60]2[C:64](=[CH:65][CH:66]=1)[N:63]([CH2:67][CH2:68][C:69]1[CH:70]=[N:71][C:72]([C:75]([F:78])([F:77])[F:76])=[CH:73][CH:74]=1)[CH:62]=[C:61]2[CH2:79][CH2:80][NH:81][CH3:82].C=O.C(O)(C(F)(F)F)=O>C(#N)C.C(N(CC)CC)C>[Cl:57][C:58]1[CH:59]=[C:60]2[C:64](=[CH:65][CH:66]=1)[N:63]([CH2:67][CH2:68][C:69]1[CH:70]=[N:71][C:72]([C:75]([F:78])([F:77])[F:76])=[CH:73][CH:74]=1)[C:62]1[CH2:82][N:81]([CH3:3])[CH2:80][CH2:79][C:61]2=1Participants
10
Reactant 7
HCID 712Formaldehyde
HCID 6422Trifluoroacetic acid
HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)
HCID 139945474,4-Diethoxy-N-methylbutan-1-amine
HCID 668695375-(2-Bromoethyl)-2-(trifluoromethyl)pyridine
HCID 669116401-(4-Chlorophenyl)-1-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)hydrazine
HCID 689949112-(5-chloro-1-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-1H-indol-3-yl)-N-methylethanamineProduct 1
Reagents, catalysts & solvents 2
Procedure
The title compound is prepared by following General Methods 1, 3 and 4 using 4-chlorophenylhydrazine hydrochloride, 5-(2-bromoethyl)-2-(trifluoromethyl)pyridine, and triethylamine (General Method 1), 1-(4-chlorophenyl)-1-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)hydrazine and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3) and 2-(5-chloro-1-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-1H-indol-3-yl)-N-methylethanamine, formaldehyde and TFA in acetonitrile (General Method 4).
Sources & evidence
- ORD record
- ord-093a86622acf43b7ac7b30a8b67ce7fb
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260429B2
Reaction notes
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