Lithium hydroxide, monohydrate → 3-(4-Fluoro-phenyl)-1-methyl-1H-indole-6-carboxylic acid

HRID 2365344Notes

Reaction equation

HRID 2365344 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19]C)=[O:18])=[CH:14][CH:15]=3)[N:10]([CH3:21])[CH:9]=2)=[CH:4][CH:3]=1.O[Li].O>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=3)[N:10]([CH3:21])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59625676Methyl 3-(4-fluorophenyl)-1-methyl-1H-indole-6-carboxylate

Product 1

HCID 596257173-(4-Fluoro-phenyl)-1-methyl-1H-indole-6-carboxylic acidYield 100.6%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution compound 53f (264 mg, 0.93 mmol), and LiOH.H2O (156.4 mg, 3.73 mmol) in THF/H2O (10 mL/10 mL) was stirred at 45° C. for 5 h. The resulting mixture was concentrated and diluted with water. The water layer was acidified with 1N aqueous HCl to pH˜4 and extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated to give compound 53g (252 mg), which was used in the next reaction without further purification. MS m/z (M+H+) 270.1.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-95d58a8bc44f43b2a8389cfa5cb67264
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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