Potassium Hydroxide → 5-(2-(1,2,3,4-Tetrahydro-8-(hydroxymethyl)-2-methylpyrido[4,3-b]indol-5-yl)ethyl)pyridine-2-carboxylic acid

HRID 574584Notes

Reaction equation

HRID 574584 reaction equation
[CH3:1][N:2]1[CH2:16][CH2:15][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH2:13][OH:14])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[CH:17]([C:19]1[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[N:23][CH:24]=1)=[CH2:18].[OH-].[K+]>CN1C(=O)CCC1>[OH:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:18][CH2:17][C:19]3[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[N:23][CH:24]=3)[C:5]3[CH2:15][CH2:16][N:2]([CH3:1])[CH2:3][C:4]=3[C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 230615385-Ethenylpyridine-2-carboxylic acidHCID 68761666(2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indol-8-yl)methanol

Product 1

HCID 578762655-(2-(1,2,3,4-Tetrahydro-8-(hydroxymethyl)-2-methylpyrido[4,3-b]indol-5-yl)ethyl)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The title compound is prepared from a mixture of (2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indol-8-yl)methanol, 5-vinylpyridine-2-carboxylic acid and KOH (5-7 equiv) in NMP at a temperature ranging between 25 deg C. to 100 deg C. The product obtained is isolated by preparative HPLC.

Workup

  1. customranging between 25 deg C
  2. customto 100 deg C
  3. customThe product obtained
  4. customis isolated by preparative HPLC

Sources & evidence

ORD record
ord-b6f781e597394524b81feffe2009b8f4
Source dataset
uspto-grants-2015_05
Patent number
US09034880B2

Reaction notes

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