Hydrochloric Acid → 2-(3-Fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carboxylic acid

HRID 1963093Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:6]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[CH3:28])=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[CH:9]2)=[O:4].[OH-].[Na+].Cl>O1CCOCC1>[F:27][C:23]1[C:22]([CH3:28])=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][C:6]1[C:5]([C:3]([OH:4])=[O:2])=[C:13]2[N:8]([C:7]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:9]=[CH:10][CH:11]=[CH:12]2

Participants

Conditions

Temperature: 90 °C

Procedure

The compound of step 3 (250 mg, 0.67 mmol) was dissolved in dioxane (10 ml) and treated with 10 ml of an aqueous 10 N solution of sodium hydroxide. The mixture was heated to 90° C. for 12 h, cooled to room temperature and neutralized with dilute hydrochloric acid. The aqueous phase was extracted with DCM and the combined organic phases dried over sodium sulfate and filtered. The solution was evaporated to give 258 mg of the crude title compound which was used in the next step without purification.

Workup

extractionThe aqueous phase was extracted with DCM
dry with materialthe combined organic phases dried over sodium sulfate
filtrationfiltered
customThe solution was evaporated

Sources & evidence

ORD record: ord-282d5eabf8f34b50a4713a5a2e1d6c4d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415336B2

Reaction notes

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