Methanol → 5-Hydroxy-1-(2,2,2-trifluoro-ethyl)-1H-indole-2-carboxylic acid

HRID 132813Notes

Reaction equation

HRID 132813 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]([F:20])([F:19])[F:18])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])C.O.[OH-].[Li+].O.CO>O1CCCC1>[OH:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:16][C:17]([F:20])([F:18])[F:19])[C:6]([C:4]([OH:5])=[O:3])=[CH:14]2

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 24985291Ethyl 5-hydroxy-1-(2,2,2-trifluoroethyl)-1H-indole-2-carboxylate2×

Product 1

HCID 675268895-Hydroxy-1-(2,2,2-trifluoro-ethyl)-1H-indole-2-carboxylic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-hydroxy-1-(2,2,2-trifluoro-ethyl)-1H-indole-2-carboxylic acid ethyl ester (Intermediate 1, step b, 8.5 g, 1.0 eq.), lithium hydroxide monohydrate (1.43 g, 1.15 eq.), water (45 mL), methanol (30 mL) and tetrahydrofuran (90 mL) was heated to reflux for 24 h. The volatiles were removed in vacuo and the resulting solution was acidified (pH ca. 2) with hydrochloric acid (1N). The precipitate was filtered and dried in vacuo to yield 7.65 g (99%) of the desired product as off-white solid. MS (m/e): 258.5 (M−H−, 100%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. customThe volatiles were removed in vacuo
  4. filtrationThe precipitate was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-abefd06ebbf7415198202f4f7f1d9d20
Source dataset
uspto-grants-2008_06
Patent number
US07388095B2

Reaction notes

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