Potassium Hydroxide → 5-(2-(6-carboxypyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole-8-carboxylic acid

HRID 710906Notes

Reaction equation

HRID 710906 reaction equation
[CH3:1][N:2]1[CH2:17][CH2:16][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([C:13]([OH:15])=[O:14])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[CH:18]([C:20]1[CH:21]=[CH:22][C:23]([C:26]([OH:28])=[O:27])=[N:24][CH:25]=1)=[CH2:19].[OH-].[K+]>CN1C(=O)CCC1>[C:26]([C:23]1[N:24]=[CH:25][C:20]([CH2:18][CH2:19][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([C:13]([OH:15])=[O:14])=[CH:11][C:12]=3[C:4]3[CH2:3][N:2]([CH3:1])[CH2:17][CH2:16][C:5]2=3)=[CH:21][CH:22]=1)([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2182822-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acidHCID 230615385-Ethenylpyridine-2-carboxylic acid

Product 1

HCID 578760225-(2-(6-carboxypyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole-8-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]indole-8-carboxylic acid, 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-14f628cf05a34e0e9df6b1f86f18232e
Source dataset
uspto-grants-2015_11
Patent number
US09181240B2

Reaction notes

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