반응식
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]=1참가 물질
반응물 5
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- 85 °C
실험 절차
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).
후처리
- customThe mixture was degassed with N2
- filtrationthen filtered
- washThe residue was washed with DMSO (2 mL)
- customthe filtrate purified by reverse phase preparative HPLC
출처 및 근거
- ORD 기록
- ord-bbc7da129029491fa8c2b79debaa811c
- 출처 데이터셋
- uspto-grants-2009_12
- 특허 번호
- US07635695B2
연결된 노트
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