Ethyl bromoacetate → Ethyl 2-(1-p-tolylhydrazinyl)acetate

HRID 2198310Notes

Reaction equation

[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([NH:7][NH2:8])=[CH:3][CH:2]=1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>>[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([N:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH2:8])=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 10875(4-Methylphenyl)hydrazine

Product 1

HCID 57930412Ethyl 2-(1-p-tolylhydrazinyl)acetate

Procedure

Method for the preparation of compound 19 [isopentyl 2-(2,6-dimethyl-3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)acetate]: p-tolylhydrazine is alkylated with ethyl 2-bromoacetate to give the substituted phenylhydrazine, ethyl 2-(1-p-tolylhydrazinyl)acetate (III). The reaction of III with 4,4-dimethoxy-N-methylbutan-1-amine gives the indole derivative ethyl 2-(5-methyl-3-(2-(methylamino)ethyl)-1H-indol-1-yl)acetate (V). Effecting the indole to standard Pictet Spingler conditions with formaldehyde gives the 1-carboline intermediate (VI) ethyl 2-(2,6-dimethyl-3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)acetate. Following treatment of VI with base the acid (VIII) 2-(2,6-dimethyl-3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)acetic acid is obtained. The treatment of this acid with DCC or other standard coupling reagents with 3-methylbutan-1-ol gives compound 19 isopentyl 2-(2,6-dimethyl-3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)acetate. After the successful synthesis of the compound, purification can be achieved using standard normal phase or reverse phase methods.

Sources & evidence

ORD record: ord-61fe32d81af34031bc3a3af22ba2a069
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338447B2

Reaction notes

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