Tris(furan-2-yl)phosphane → [7-(3,6-dihydro-2H-pyran-4-yl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester

HRID 1611937Notes

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.C([Sn](CCCC)(CCCC)[C:23]1[CH2:24][CH2:25][O:26][CH2:27][CH:28]=1)CCC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[O:6][C:7]2[C:13]([C:23]3[CH2:28][CH2:27][O:26][CH2:25][CH:24]=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 350 g (10.1 mmol) (7-iodo-4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester in 50 ml dioxane were added 5.63 g (15.1 mmol) tributyl-(3,6-dihydro-2H-pyran-4-yl)-stannane, 173 mg (0.30 mmol) bis(dibenzylideneacetone)palladium(0), 374 mg (1.61 mmol) tri(2-furyl)phospine. The mixture was heated at 100° C. for 22 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. Flash chromatography (2/98 methanol/dichloromethane then 5/95 methanol/dichloromethane) followed by trituration in dichloromethane afforded 1.30 g (42%) [7-(3,6-dihydro-2H-pyran-4-yl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester as a white solid. ES-MS m/e (%): 305 (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-faebdaf524424a6ca0ef2b187b7fb512
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06992083B2

Reaction notes

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