Naratriptan → HCID 86670066, compound

HRID 1028409Notes

Reaction equation

HRID 1028409 reaction equation
CNS(CC[C:8]1[CH:9]=[CH:10][C:11]2[NH:16][CH:15]=[C:14](C3CCN(C)CC3)[C:12]=2[CH:13]=1)(=O)=O.Br[C:25]1[CH:26]=C2[C:31](=[CH:32][CH:33]=1)[NH:30][CH:29]=C2.CN1CCC(=[O:41])CC1.[OH-].[K+]>CO>[OH:41][CH:31]1[CH2:32][CH:33]([C:13]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:12]=2[CH:14]=[CH:15][NH:16]3)[CH2:25][CH2:26][N:30]1[CH3:29]

Participants

6

Reactant 4

HCID 4440NaratriptanHCID 14797Potassium HydroxideHCID 249055-BromoindoleHCID 740491-Methyl-4-piperidone

Product 1

HCID 86670066HCID 86670066, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

U.S. Pat. No. 4,997,841 discloses naratriptan, its salts and several processes for its preparation. One of the processes comprises reacting 5-bromoindole with 1-methylpiperidin-4-one by means of KOH in methanol at room temperature to give 5-bromo-3-(4-(hydroxy-1-methylpiperidin-4-yl)-1H-indole, which is condensed with N-methylvinylsulfonamide by means of palladium acetate and tri-p-tolyl phosphine in hot DMF to afford (E)-N-methyl-2-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]vinylsulfonamide. Finally, this compound is hydrogenated with H2 over Pd/C to obtain naratriptan.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-4d8e9d0540194d3384fe35e51c93d3dc
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

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