Methanol → 5-(1-isopropyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid

HRID 901088Notes

Reaction equation

C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH:16]1[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17]1)=[CH:10][CH:9]=2)=[O:5])C.O.[OH-].[Li+].CO>O>[CH:21]([N:18]1[CH2:19][CH2:20][CH:16]([O:15][C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]3)[CH2:17]1)([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2.05 g (6 mmol) 5-(1-Isopropyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid ethyl ester and 0.299 g (7 mmol) lithiumhydroxide monohydrate 30 ml THF, 30 ml methanol and 15 ml water was heated to 100° C. for 2 h. The organic solvents were removed and aq. 1N HCl was added to adjust the pH of the solution to 2-3. Subsequently, the mixture was evaporated to dryness and the mixture was used without further purification in the next step. MS (m/e): 289.1 (MH+, 100%).

Workup

customThe organic solvents were removed
additionaq. 1N HCl was added
customSubsequently, the mixture was evaporated to dryness
customthe mixture was used without further purification in the next step

Sources & evidence

ORD record: ord-542b57c442ff4f9290437e56c4dfc2d3
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361682B2

Reaction notes

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