1-bromo-3-methylsulfanyl-6,7-dihydro-5H-2-benzothiophen-4-one → 3-Methylthio-1-(oxazol-2-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one
Reaction equation
Br[C:2]1[S:3][C:4]([S:12][CH3:13])=[C:5]2[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:6]=12.C([Sn](CCCC)(CCCC)[C:19]1[O:20][CH:21]=[CH:22][N:23]=1)CCC>>[CH3:13][S:12][C:4]1[S:3][C:2]([C:19]2[O:20][CH:21]=[CH:22][N:23]=2)=[C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:5]=12Participants
3
Procedure
In a similar way to that in Example 35, using 1-bromo-3-methylthio-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one and 2-(tri-n-butylstannyl)oxazole, the title compound was isolated as a pale yellow solid (35 mg, 37%). mp 157-159° C. Found: C, 54.0; H, 3.7; N, 5.6%. C12H11NO2S2 requires: C, 54.32; H, 4.18; N, 5.28%. 1HNMR (250 MHz, CDCl3) δ 2.05-2.16 (2H, m), 2.56-2.61 (2H, m), 2.63 (3H, s), 3.20-3.25 (2H, m), 7.20 (1H, s), 7.66 (1H, s). MS (ES+) 266 (M+1).
Sources & evidence
- ORD record
- ord-df2a7deb411a44c1982c62b19acdaf91
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06262103B1
Reaction notes
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