4-Fluorophenylboronic acid → [7-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester

HRID 1611948Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[O:6][C:7]2[C:13](I)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1.[Cl-].[Li+].[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.COCCOC>[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[O:6][C:7]2[C:13]([C:24]3[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=3)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 3.00 g (8.62 mmol) (7-iodo-4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester in 20 ml dioxane and 60 ml 1,2-dimethoxyethane were added 731 mg (17.2 mmol) lithium chloride, 299 mg (0.26 mmol) tetrakis(triphenyl-phosphine)palladium(0), 1.45 g (10.3 mmol) para-fluorobenzeneboronic acid and 18 ml of a 1 N aq. solution of sodium bicarbonate. The mixture was heated at 100° C. for 24 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Trituration in ether afforded 2.67 g (98%) [7-(4-fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester as an off-white solid. ES-MS m/e (%): 317 (M+H+, 100).

Workup

additionpoured onto water
extractionextracted three times with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fe8ce4dcce184b8883c3347b16d85a35
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06992083B2

Reaction notes

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