Sodium Hydroxide → 6-((6-chloro-2-cyclopropyl-1-(1-ethyl-1H-pyrazol-4-yl)-7-fluoro-1H-indol-3-yl)thio)picolinic Acid

HRID 522779Notes

Reaction equation

[Cl:1][C:2]1[C:10]([F:11])=[C:9]2[C:5]([C:6]([S:22][C:23]3[N:28]=[C:27]([C:29]([O:31]C)=[O:30])[CH:26]=[CH:25][CH:24]=3)=[C:7]([CH:19]3[CH2:21][CH2:20]3)[N:8]2[C:12]2[CH:13]=[N:14][N:15]([CH2:17][CH3:18])[CH:16]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[C:10]([F:11])=[C:9]2[C:5]([C:6]([S:22][C:23]3[N:28]=[C:27]([C:29]([OH:31])=[O:30])[CH:26]=[CH:25][CH:24]=3)=[C:7]([CH:19]3[CH2:20][CH2:21]3)[N:8]2[C:12]2[CH:13]=[N:14][N:15]([CH2:17][CH3:18])[CH:16]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of compound 9 (2.81 g, 5.97 mmol) in THF:water (4:1) (40 mL) was added 1M aq. NaOH solution (6.03 mL, 6.03 mmol) and the mixture was heated at 60° C. for 1 h. After completion of the reaction, the solvent was removed to afford Compound 1-92 (2.83 g, 100%) as a light brown solid. LC-MS: 457 (M++1).

Workup

customAfter completion of the reaction
customthe solvent was removed

Sources & evidence

ORD record: ord-660676f18f90448396c0b19c01214e10
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334261B2

Reaction notes

Loading…