Beta-Carboline → Dicyclohexylcarbodiimide

HRID 2198311Notes

Reaction equation

HRID 2198311 reaction equation
C1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3]N=1.[CH3:14][N:15]1[CH2:27][CH2:26][C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:28])[CH:23]=3)[N:18]([CH2:29][C:30]([OH:32])=[O:31])[C:17]=2[CH2:16]1>CC(C)CCO>[CH2:22]1[CH2:23][CH2:24][CH:19]([N:18]=[C:13]=[N:12][CH:11]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:20][CH2:21]1.[CH3:14][N:15]1[CH2:27][CH2:26][C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:28])[CH:23]=3)[N:18]([CH2:29][C:30]([O:32][CH2:3][CH2:4][CH:5]([CH3:6])[CH3:13])=[O:31])[C:17]=2[CH2:16]1

Participants

5

Reactant 2

HCID 64961Beta-CarbolineHCID 442426452-(1,2,3,4-Tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetic acid

Product 2

HCID 10868DicyclohexylcarbodiimideHCID 57930375Isopentyl 2-(1,2,3,4-tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetate

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

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.

Workup

  1. customis obtained

Sources & evidence

ORD record
ord-5708e8c3f6e8461f8b4d2989694a2745
Source dataset
uspto-grants-2012_12
Patent number
US08338447B2

Reaction notes

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