Lithium Hydroxide → HCID 71078000, compound

HRID 1774482Notes

Reaction equation

HRID 1774482 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:7]=[N:6][CH:5]=1.[Li+].[OH-]>CO.C1COCC1.CCOC(C)=O>[Cl:20][C:16]1[CH:15]=[C:14]2[C:19]([C:11]([S:10][C:8]3[CH:7]=[N:6][CH:5]=[C:4]([CH:9]=3)[C:3]([OH:22])=[O:2])=[C:12]([CH3:21])[NH:13]2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 71077997HCID 71077997, compound

Product 1

HCID 71078000HCID 71078000, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

5-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-nicotinic acid methyl ester (0.050 g, 0.15 mmol) was dissolved in MeOH:THF (1:1, 4 mL) and LiOH (1 M aq., 1 mL) was added. The reaction was heated to 50° C. for 3.5 hours then cooled. The reaction was acidified with HCL (1 M aq., 1 mL), diluted with EtOAc, dried over MgSO4, then filtered and concentrated to supply the title compound. Mass spectrometric data: [M+H]+=319.

Workup

  1. temperaturethen cooled
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to supply the title compound

Sources & evidence

ORD record
ord-319256c9577c42f1a89b31d408cc1e37
Source dataset
uspto-grants-2016_02
Patent number
US09260416B2

Reaction notes

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