2-Benzothiazolamine, 6-bromo- → 6-(3-Fluoro-4-methoxyphenyl)benzo[d]thiazol-2-amine
Reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=1.[F:12][C:13]1[CH:14]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]>>[F:12][C:13]1[CH:14]=[C:15]([C:2]2[CH:11]=[CH:10][C:5]3[N:6]=[C:7]([NH2:9])[S:8][C:4]=3[CH:3]=2)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]Participants
3
Procedure
Compound 6-(3-fluoro-4-methoxyphenyl)benzo[d]thiazol-2-amine (W143) was prepared using the general procedure for Suzuki coupling reaction between 6-bromobenzo[d]thiazol-2-amine (75 mg, 0.3 mmol) and 2-(3-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69 mg, 0.3 mmol), as a white solid (30 mg, 36%). 1H NMR (400 MHz, acetone-d6) δ 7.92 (d, J=2.0 Hz, 1 H), 7.52 (dd, J=8.4, 2.0 Hz, 1 H), 7.47-7.24 (m, 3 H), 7.20 (t, J=8.4 Hz, 1 H), 6.86 (brs, 2 H), 3.92 (s, 3 H); MS (ESI) m/z 275 (M+H+).
Sources & evidence
- ORD record
- ord-72478752899642f1966946c613c65ced
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420052B2
Reaction notes
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