Formaldehyde → 6-chloro-9-((1-(4-fluorophenyl)cyclopropyl)methyl)-2,3,4,9-tetrahydro-2-methyl-1H pyrido[3,4-b]indole

HRID 1775919Notes

Reaction equation

HRID 1775919 reaction equation
Cl.ClC1C=CC(NN)=CC=1.BrCC1(C2C=CC(F)=CC=2)CC1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]([CH2:32][C:33]2([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[CH2:35][CH2:34]2)N)=[CH:26][CH:25]=1.C(OC(OCC)CCCNC)C.ClC1C=C2[C:62](=CC=1)[N:61]([CH2:65][C:66]1([C:69]3[CH:74]=[CH:73]C(F)=CC=3)CC1)C=C2CCNC.C=O.C(O)(C(F)(F)F)=O>C(#N)C.C(N(CC)CC)C>[Cl:23][C:24]1[CH:29]=[C:28]2[C:27](=[CH:26][CH:25]=1)[N:30]([CH2:32][C:33]1([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[CH2:35][CH2:34]1)[C:74]1[CH2:73][N:61]([CH3:62])[CH2:65][CH2:66][C:69]2=1

Participants

10

Reactant 7

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 139945474,4-Diethoxy-N-methylbutan-1-amineHCID 669116611-[1-(Bromomethyl)cyclopropyl]-4-fluorobenzeneHCID 669116911-(4-Chlorophenyl)-1-((1-(4-fluorophenyl)cyclopropyl)methyl)hydrazineHCID 689930602-(5-chloro-1-((1-(4-fluorophenyl)cyclopropyl)methyl)-1H-indol-3-yl)-N-methylethanamine

Product 1

HCID 579303656-chloro-9-((1-(4-fluorophenyl)cyclopropyl)methyl)-2,3,4,9-tetrahydro-2-methyl-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 by) using 4-chlorophenylhydrazine hydrochloride, 1-(1-(bromomethyl)cyclopropyl)-4-fluorobenzene, and triethylamine (General Method 1), 1-(4-chlorophenyl)-1-((1-(4-fluorophenyl)cyclopropyl)methyl)hydrazine and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3) and 2-(5-chloro-1-((1-(4-fluorophenyl)cyclopropyl)methyl)-1H-indol-3-yl)-N-methylethanamine, formaldehyde and TFA in acetonitrile (General Method 4).

Sources & evidence

ORD record
ord-ea3dda514537457a89a794a0c4ecd134
Source dataset
uspto-grants-2016_02
Patent number
US09260429B2

Reaction notes

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