Sodium Hydroxide → HCID 178518886, compound

HRID 634164Notes

Reaction equation

HRID 634164 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]3[S:19][C:20](S(C)(=O)=O)=[N:21][N:22]=3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.[OH-:37].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]3[S:19][C:20]([OH:37])=[N:21][N:22]=3)[CH:16]=2)[NH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 683286122-(3-(2,4-difluorophenyl)-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole

Product 1

HCID 178518886HCID 178518886, compoundYield 11.28%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(3-(2,4-difluorophenyl)-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole (0.010 g, 0.018 mmol), dioxane (0.5 mL), and NaOH (1 M, 0.1 mL) was heated in a Biotage microwave for 10 min at 100° C., then at 120° C. for an additional 10 min. The mixture was purified by preparative HPLC (20-90% AcCN/H2O/0.1% TFA) to give 5-(3-(2,4-difluorophenyl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-ol (1 mg, 2.068 μmol, 11.28%). MS (ESI, pos. ion) m/z: 330 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 7.99 (1H, s), 7.67-7.75 (1H, m), 7.53-7.64 (3H, m), 7.07-7.15 (2H, m).

Workup

  1. customThe mixture was purified by preparative HPLC (20-90% AcCN/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-75f68e3f11094fb9ad60341b1d826a9f
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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