6-(Methoxycarbonyl)-7-fluorobenzo[d]thiazole-2-thiolate potassium salt → Methyl 7-fluoro-2-(methylthio)benzo[d]thiazole-6-carboxylate
Reaction equation
[K+].[CH3:2][O:3][C:4]([C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([S-:13])[S:12][C:8]=2[C:7]=1[F:16])=[O:5].[K].S[C:19]1SC2C(N=1)=NC=C(C(OCC)=O)C=2>>[F:16][C:7]1[C:8]2[S:12][C:11]([S:13][CH3:19])=[N:10][C:9]=2[CH:14]=[CH:15][C:6]=1[C:4]([O:3][CH3:2])=[O:5]Participants
3
Procedure
Methyl 7-fluoro-2-(methylthio)benzo[d]thiazole-6-carboxylate was synthesized as a clear oil (400 mg, 29%) using a procedure analogous to that described in Step 2 of Example 114, substituting 6-(methoxycarbonyl)-7-fluorobenzo[d]thiazole-2-thiolate potassium salt from the previous step for ethyl 2-mercaptothiazolo[4,5-b]pyridine-6-carboxylate potassium salt used in Example 114. 1H NMR (500 MHz, DMSO-d6) δ 7.96 (m, 1H), 7.77 (d, J=8.6 Hz, 1H), 3.89 (s, 3H), 2.85 (s, 3H); LCMS (ESI) m/z 258 (M+H)+.
Sources & evidence
- ORD record
- ord-ffad8b2be5c6483d95ac421e0e1f35be
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952058B2
Reaction notes
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