N2-(4-bromo-2-fluorophenyl)-1,3-benzothiazol-2-amine → N2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzothiazol-2-amine
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[C:4]([F:18])[CH:3]=1.FC1C=C([B:26]2[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]2)C=CC=1NC1OC2C=CC=CC=2N=1>>[F:18][C:4]1[CH:3]=[C:2]([B:26]2[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]2)[CH:7]=[CH:6][C:5]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1Participants
3
Procedure
N2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzothiazol-2-amine was prepared from N2-(4-bromo-2-fluorophenyl)-1,3-benzothiazol-2-amine (1.699 g, 5.258 mmol) in a manner similar to that used for N2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazol-2-amine. The compound was formed as an off-white powder (0.825 g, 42%). RP-HPLC (25 to 100% CH3CN in 0.1 N aqueous ammonium acetate over 10 min at 1 mL/min using a Hypersil HS C18, 250×4.6 mm column) tr=14.48 min, 90%; m/z 371 (MH+).
Sources & evidence
- ORD record
- ord-1f8c9796b74742efb101eb76edaf288e
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06921763B2
Reaction notes
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