Tris(furan-2-yl)phosphane → [7-(5,6-Dihydro-[1,4]dioxin-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid ethyl ester

HRID 985800Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:18])[NH:5][C:6]1[S:7][C:8]2[C:14](I)=[CH:13][CH:12]=[C:11]([O:16][CH3:17])[C:9]=2[N:10]=1)[CH3:2].C([Sn](CCCC)(CCCC)[C:24]1[O:25][CH2:26][CH2:27][O:28][CH:29]=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]>[CH2:1]([O:3][C:4](=[O:18])[NH:5][C:6]1[S:7][C:8]2[C:14]([C:24]3[O:25][CH2:26][CH2:27][O:28][CH:29]=3)=[CH:13][CH:12]=[C:11]([O:16][CH3:17])[C:9]=2[N:10]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 5.0 g (13.2 mmol) (7-iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid ethyl ester in 60 ml dioxane were added 6.94 g (18.5 mmol) tributyl-(5,6-dihydro-[1,4]dioxin-2-yl)-stannane, 456 mg (0.79 mmol) bis(dibenzylideneacetone)palladium and 491 mg (2.12 mmol) trifurylphosphine. The mixture was heated at 100° C. for 3 h, then cooled to room temperature and concentrated in vacuo. Flash chromatography (5/95 acetone/dichloromethane) afforded 4.00 g (90%) [7-(5,6-dihydro-[1,4]dioxin-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid ethyl ester as a light yellow foam. ES-MS m/e (%): 337 (M+H+, 100).

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3ee619eb784d438b812eb030e260a83c
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872833B2

Reaction notes

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