Hydrochloric Acid → 7-Bromo-2-(3-fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carboxylic acid

HRID 1963097Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:6]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=2[CH3:29])=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[C:13]=1[CH:12]=[C:11]([Br:14])[CH:10]=[CH:9]2)=[O:4].[OH-].[Na+].Cl>O1CCOCC1>[Br:14][C:11]1[CH:10]=[CH:9][N:8]2[C:13]([CH:12]=1)=[C:5]([C:3]([OH:4])=[O:2])[C:6]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[CH3:29])=[C:7]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

The compound of step 1 (450 mg, 0.99 mmol) was dissolved in 1,4-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 phase were dried over sodium sulfate. The crude title product obtained after evaporation was used without purification in the next step.

Workup

extractionThe aqueous phase was extracted with DCM
dry with materialthe combined organic phase were dried over sodium sulfate

Sources & evidence

ORD record: ord-662cf9e08e8f4a72b97ca9403685283e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415336B2

Reaction notes

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