反応式
Br[C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][S:7](=[O:10])(=[O:9])[CH2:8][C:4]=2[CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.CC([O-])=O.[K+].C([O-])([O-])=O.[K+].[K+].[NH2:42][C:43]1[C:48]2[CH:49]=[C:50](Br)[S:51][C:47]=2[C:46]([C:53]([NH2:55])=[O:54])=[CH:45][N:44]=1>CS(C)=O.O>[NH2:42][C:43]1[C:48]2[CH:49]=[C:50]([C:2]3[CH:12]=[CH:11][CH:5]4[CH2:6][S:7](=[O:10])(=[O:9])[CH2:8][CH:4]4[CH:3]=3)[S:51][C:47]=2[C:46]([C:53]([NH2:55])=[O:54])=[CH:45][N:44]=1参加物
反応物 5
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 85 °C
実験手順
To a stirred solution 5-bromo-1,3-dihydro-benzo[c]thiophene 2,2-dioxide (160 mg, 0.65 mmol) 67 (Salor, Milwaukee, Wis.) in DMSO (1 mL) was added bis(pinacolato)diboron (178 mg, 0.70 mmol), KOAc (159 mg, 1.6 mmol) and Pd(dppf)Cl2 DCM complex (22 mg, 0.027 mmol). The mixture was degassed with N2 and heated at 85° C. for 2 h then DMSO (2 mL), H2O (0.5 mL), K2CO3 (223 mg, 1.6 mmol) and 4-amino-2-bromo-thieno[3,2-c]pyridine-7-carboxylic acid amide H2SO4 salt 17 (200 mg, 0.54 mmol) were added. The mixture was stirred at 85° C. for a further 12 h then filtered. The residue was washed with DMSO (2 mL) and the filtrate purified by reverse phase preparative HPLC to yield 68 as a white solid. 1H-NMR (400 MHz, d6-DMSO) δ 8.31 (s, 1H), 8.24 (s, 1H), 8.19 (bs, 1H), 7.97–7.92 (m, 3H), 7.85 (d, 1H), 4.78 (s, 2H), 4.71 (s, 2H).
後処理
- customThe mixture was degassed with N2
- filtrationthen filtered
- washThe residue was washed with DMSO (2 mL)
- customthe filtrate purified by reverse phase preparative HPLC
出典と根拠
- ORDレコード
- ord-6413c8b5201b434daf564432eb617312
- 出典データセット
- uspto-grants-2007_04
- 特許番号
- US07199119B2
関連ノート
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