Triethylamine → [7-(5,6-Dihydro-[1,4]dioxin-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyl ester

HRID 985784Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[S: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[O:24][CH2:25][CH2:26][O:27][CH:28]=1)CCC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(N(CC)CC)C>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[S:6][C:7]2[C:13]([C:23]3[O:24][CH2:25][CH2:26][O:27][CH:28]=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 13.0 g (35.7 mmol) (7-iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester in 200 ml dioxane were added 20.1 g (53.6 mmol) tributyl-(5,6-dihydro-[1,4]dioxin-2-yl)-stannane, 616 mg (1.07 mmol) bis(dibenzylideneacetone)palladium, 1.33 g (5.71 mmol) trifurylphosphine and 7.46 ml (53.6 mmol) triethylamine. The mixture was heated at 100° C. for 16 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 (1/4-1/2 acetone/hexane) followed by trituration in ether afforded 5.20 g (45%) [7-(5,6-dihydro-[1,4]dioxin-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyl ester as a white solid. ES-MS m/e (%): 323 (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-074816d92169436aa3536181de7150bb
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872833B2

Reaction notes

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