Pyridine → HCID 10430277, compound

HRID 1034438Notes

Reaction equation

[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].[C:21]1([CH3:31])[CH:26]=CC(S(Cl)(=O)=O)=C[CH:22]=1.C(O)(C)(C)C.N1C=CC=CC=1>CCOCC>[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([O:16][C:21]([CH3:31])([CH3:26])[CH3:22])=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2-(3-bromo-5-methyl-2-benzofuranyl)benzoic acid (described in EP-A-0434249) (2.0 g), p-toluenesulphonyl chloride (2.5 g), tert-butanol (10 ml) and pyridine (3 ml) was stirred at 0° C. and allowed to warm to room temperature. Stirring was continued for 72 hours. The mixture was then diluted with ether (100 ml) and washed with 2M hydrochloric acid (75 ml) followed by an aqueous solution of 1M sodium bicarbonate (75 ml). The aqueous solutions were further extracted with ethyl acetate (100 ml) and the combined organic extracts were dried and evaporated in vacuo. Purification by flash column chromatography eluting with dichloromethane:hexane (3:7) gave the title compound (0.6 g) as a colourless gum.

Workup

temperatureto warm to room temperature
stirringStirring
washwashed with 2M hydrochloric acid (75 ml)
extractionThe aqueous solutions were further extracted with ethyl acetate (100 ml)
customthe combined organic extracts were dried
customevaporated in vacuo
customPurification by flash column chromatography
washeluting with dichloromethane:hexane (3:7)

Sources & evidence

ORD record: ord-06af9d81acd0477691eee3120c2adbe3
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05317023

Reaction notes

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