Ethyl 2-(methylsulfanyl)-1,3-benzothiazole-6-carboxylate → (7-Fluoro-2-(methylthio)benzo[d]thiazol-6-yl)methanol
Reaction equation
[F:1][C:2]1[C:10]2[S:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:13](OC)=[O:14].CSC1SC2C=C(C(OCC)=O)C=CC=2N=1>>[F:1][C:2]1[C:10]2[S:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:13][OH:14]Participants
3
Procedure
(7-Fluoro-2-(methylthio)benzo[d]thiazol-6-yl)methanol was synthesized as a white solid (249 mg, 69%) using a procedure analogous to that described in Step 3 of Example 36, substituting methyl 7-fluoro-2-(methylthio)benzo[d]thiazole-6-carboxylate from the previous step for ethyl 2-(methylthio)benzo[d]thiazole-6-carboxylate used in Example 36. 1H NMR (500 MHz, DMSO-d6) δ 7.70 (d, J=8.4 Hz, 1H), 7.56 (t, J=7.8 Hz, 1H), 5.39 (t, J=5.8 Hz, 1H), 4.64 (d, J=5.7 Hz, 2H), 2.81 (s, 3H); LCMS (ESI) m/z 230 (M+H)+.
Sources & evidence
- ORD record
- ord-3ff9e12ec2144ea5977282ce47838385
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952058B2
Reaction notes
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