반응식
Br[CH2:2][C:3]1[O:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[CH2:25][C@H:24]([NH:29][S:30]([CH:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])[CH2:23]3)O1>C1COCC1>[F:9][C:8]([F:11])([F:10])[C:5]1[O:4][C:3]([CH2:2][C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[CH2:25][C@H:24]([NH:29][S:30]([CH:33]([CH3:35])[CH3:34])(=[O:31])=[O:32])[CH2:23]3)=[CH:7][CH:6]=1참가 물질
반응물 2
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- 100 °C
실험 절차
2-(bromomethyl)-5-(trifluoromethyl)furan (0.123 mmol, 28.2 mg), (S)—N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (0.123 mmol, 45 mg) and Bromo(N-succinimidyl)bis-(triphenylphosphine)palladium(II) (6.16 μmol, 4.98 mg) were suspended in THF (1 mL) and 2M NaCO3 (0.5 mL) added. The mixture was heated to 100° C. for 10 min. After this time the reaction mixture was irradiated for a further 20 min at 100° C. before standing overnight. The mixture was concentrated to remove THF before partitioning between DCM/H2O. The organic layer was collected and dried using a hydrophobic filter tube. Concentration and purification on basic HPLC gave the title compound (7.5 mg, 0.019 mmol, 15.7%). MS (ESI): m/z [M−H]− 386.3.
후처리
- customAfter this time the reaction mixture was irradiated for a further 20 min at 100° C.
- concentrationThe mixture was concentrated
- customto remove THF
- custombefore partitioning between DCM/H2O
- customThe organic layer was collected
- customdried
- concentrationConcentration and purification on basic HPLC
출처 및 근거
- ORD 기록
- ord-50700ac2a7d9403bbe0aea0435ab9857
- 출처 데이터셋
- uspto-grants-2013_09
- 특허 번호
- US08536214B2
연결된 노트
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