Formaldehyde → Isopentyl 2-(1,2,3,4-tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetate
Reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C[C:19]1[CH:24]=[CH:23][C:22]([N:25]([CH2:27]C(OCC)=O)N)=C[CH:20]=1.C(O[CH:36](OCC)[CH2:37][CH2:38]CNC)C.CC1C=C2C(=CC=1)N(CC(OCC)=O)C=C2CCNC.C=O.C(O)(C(F)(F)F)=O.CC1C=C2C(=CC=1)N(CC(O)=O)C1CN(C)CCC2=1.CCN=C=NCCCN(C)C>C(#N)C.CC1C=C2C(=CC=1)N(CC(OCC)=O)C1CN(C)CCC2=1.[OH-].[Na+].CC(C)CCO.C(N(CC)CC)C>[CH3:27][N:25]1[CH2:20][CH2:19][C:24]2[C:6]3[C:5](=[CH:4][CH:3]=[C:2]([CH3:10])[CH:7]=3)[N:8]([CH2:12][C:13]([O:15][CH2:16][CH2:17][CH:37]([CH3:38])[CH3:36])=[O:14])[C:23]=2[CH2:22]1Participants
15
Reactant 9
HCID 712Formaldehyde
HCID 6422Trifluoroacetic acid
HCID 7748Ethyl bromoacetate
HCID 125044-Methylphenylhydrazine monohydrochloride
HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide
HCID 139945474,4-Diethoxy-N-methylbutan-1-amine
HCID 442426452-(1,2,3,4-Tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetic acid
HCID 57930412Ethyl 2-(1-p-tolylhydrazinyl)acetate
HCID 57930443ethyl 2-(5-methyl-3-(2-(methylamino)ethyl)-1H-indol-1-yl)acetateProduct 1
Reagents, catalysts & solvents 5
Procedure
The title compound is prepared by following General Methods 1, 3, 4, 5 and 6 by using p-tolylhydrazine hydrochloride, ethyl bromoacetate, and triethylamine (General Method 1), ethyl 2-(1-(4-methylphenyl)hydrazinyl)acetate and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3), ethyl 2-(5-methyl-3-(2-(methylamino)ethyl)-1H-indol-1-yl)acetate, formaldehyde and TFA in acetonitrile (General Method 4), ethyl 2-(6-methyl-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetate and NaOH (General Method 5), and 2-(6-methyl-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetic acid, 3-methylbutan-1-ol and EDCI (General Method 6).
Sources & evidence
- ORD record
- ord-26c3f7c7fc9d4d19adce46f4bd11344c
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338447B2
Reaction notes
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