Potassium Hydroxide → 5-((4-fluorophenyl)ethynyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid

HRID 1400628Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 5-((4-fluorophenyl)ethynyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylate (0.280 g) was dissolved in MeOH (10 mL) and added 10% aq. KOH solution (5 mL). The reaction mixture was heated at 50° C. for 48 h. Progress of the reaction was monitored by TLC and LCMS. The solvent was evaporated and the residue acidified with 1% aq. HCl solution. The solid was filtered and the residue was washed with water (2-3×). The product was washed with hexane. The product was obtained as a white solid. 1H NMR (CD3OD, freebase) δ (ppm): 8.30 (d, 1H), 8.10 (m, 1H), 7.70 (m, 3H), 7.20 (m, 2H), 4.60 (m, 2H), 3.80 (m, 2H), 3.38 (m, 2H), 3.15 (s, 3H).

Workup

customThe solvent was evaporated
filtrationThe solid was filtered
washthe residue was washed with water (2-3×)
washThe product was washed with hexane
customThe product was obtained as a white solid

Sources & evidence

ORD record: ord-4504eb2cf67b4db68f2a4087261b85c6
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906925B2

Reaction notes

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