Sodium Hydroxide → 3-chloro-4-fluoro-1-methyl-1H-indole-5-carboxylic acid

HRID 1053846Notes

Reaction equation

HRID 1053846 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14]C)=[O:13])[C:9]=2[F:11])[N:4]([CH3:16])[CH:3]=1.[OH-].[Na+]>O1CCCC1.CO.ClCCl>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([OH:14])=[O:13])[C:9]=2[F:11])[N:4]([CH3:16])[CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 90014771methyl 3-chloro-4-fluoro-1-methyl-1H-indole-5-carboxylate

Product 1

HCID 900232723-chloro-4-fluoro-1-methyl-1H-indole-5-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester thus obtained was dissolved in a mixture of tetrahydrofuran (10 mL), methanol (10 mL) and dichloromethane (3 mL). 2 M sodium hydroxide (4.31 mL) was added and the mixture stirred at room temperature for 3 h. Further 2 M sodium hydroxide (4.31 mL) was added and the reaction stirred at room temperature for 16 h. The mixture was concentrated in vacuo, diluted with water and ethyl acetate added. The resultant emulsion was acidified with 1 M hydrochloric acid (pH=2-3) and extracted with ethyl acetate. The combined ethyl acetate phases were dried and concentrated to give the title compound (0.274 g) as a pale yellow solid.

Workup

  1. stirringthe reaction stirred at room temperature for 16 h
  2. concentrationThe mixture was concentrated in vacuo
  3. additiondiluted with water and ethyl acetate
  4. additionadded
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined ethyl acetate phases were dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2dc5e20b92294d31bf735bb6f93d6faa
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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