반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([NH:11][C:12]([C:14]2[N:15]=[C:16]([CH3:19])[S:17][CH:18]=2)=[O:13])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.[CH3:32][O:33][C:34]1[CH:35]=[N:36][CH:37]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH:39]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:19][C:16]1[S:17][CH:18]=[C:14]([C:12]([NH:11][C:4]2[CH:3]=[C:2]([C:38]3[CH:37]=[N:36][CH:35]=[C:34]([O:33][CH3:32])[CH:39]=3)[CH:10]=[C:9]3[C:5]=2[CH:6]=[N:7][NH:8]3)=[O:13])[N:15]=1참가 물질
7
반응물 4
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- 150 °C
실험 절차
N-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (50 mg, 0.148 mmol), Pd(dppf)Cl2 (12 mg, 0.015 mmol), 2 M sodium carbonate (aq) (0.222 ml, 0.444 mmol), 1,4-dioxane (1 ml) and water (1 ml) were added to 3-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (42 mg, 0.178 mmol). The reaction was heated in a Biotage microwave at 150° C. for 15 mins. The reaction mixture was extracted with DCM (2×20 ml) and the separated, combined organic layer was evaporated to dryness. The residue was dissolved in MeOH:DMSO (1 ml, 1:1, v/v) and purified by MDAP (Method B). Appropriate fractions were dried under a stream of nitrogen to give title compound, 11 mg. LC/MS (Method B) Rt=0.86 mins, MH+=366.
후처리
- extractionThe reaction mixture was extracted with DCM (2×20 ml)
- customwas evaporated to dryness
- dissolutionThe residue was dissolved in MeOH
- customDMSO (1 ml, 1:1, v/v) and purified by MDAP (Method B)
- customAppropriate fractions were dried under a stream of nitrogen
출처 및 근거
- ORD 기록
- ord-6ea270da5d6b44b09336958372759c76
- 출처 데이터셋
- uspto-grants-2012_04
- 특허 번호
- US08163743B2
연결된 노트
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