Lithium Hydroxide → 4-(2-fluorophenyl)-7-(morpholine-4-carbonyl)-9H-pyrido[3,4-b]indole-1-carboxylic acid

HRID 2361245Notes

Reaction equation

HRID 2361245 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16]([C:21]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[O:22])=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:29]([O:31]CC)=[O:30])=[N:10][CH:9]=1.[Li+].[OH-]>C1COCC1.CO.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16]([C:21]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[O:22])=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:29]([OH:31])=[O:30])=[N:10][CH:9]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 67994855ethyl 4-(2-fluorophenyl)-7-(morpholine-4-carbonyl)-9H-pyrido[3,4-b]indole-1-carboxylate

Product 1

HCID 679946974-(2-fluorophenyl)-7-(morpholine-4-carbonyl)-9H-pyrido[3,4-b]indole-1-carboxylic acidYield 68.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a yellow, homogeneous solution of ethyl 4-(2-fluorophenyl)-7-(morpholine-4-carbonyl)-9H-pyrido[3,4-b]indole-1-carboxylate (0.0592 g, 0.132 mmol) in THF (2.84 mL) and MeOH (0.945 mL) was added LiOH (0.022 g, 0.529 mmol) in water (0.5 mL). After 2 hr, the reaction mixture was concentrated in vacuo, and the residue was diluted with water and acidified with 1N aq. HCl to pH ˜4 by litmus paper. The mixture was extracted with EtOAc (3×), and the organic layers were combined, dried over Na2SO4, and concentrated in vacuo to give the desired product (0.0382 g, 0.091 mmol, 68.8% yield) as a yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with water
  3. extractionThe mixture was extracted with EtOAc (3×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-644b1fdf98da49efba808414e94a0cc0
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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