Hydrochloric Acid → tert-Butyl (5-methyl-1-tosyl-1H-indol-4-yl)carbamate

HRID 2174044노트

반응식

HRID 2174044 반응식
Br[C:2]1[C:3]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.[CH3:29][B-](F)(F)F.[K+].C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+].Cl>C1(C)C=CC=CC=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>[CH3:29][C:2]1[C:3]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=1)(=[O:12])=[O:13])[CH:6]=[CH:5]2

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 23692566Potassium Trifluoro(methyl)borateHCID 86701667tert-butyl (5-bromo-1-tosyl-1H-indol-4-yl)carbamate

생성물 1

HCID 86701666tert-Butyl (5-methyl-1-tosyl-1H-indol-4-yl)carbamate

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a solution of tert-butyl (5-bromo-1-tosyl-1H-indol-4-yl)carbamate (9.95 g, 21.38 mmol) in toluene (194 mL) was added potassium methyltrifluoroborate (13 g, 107 mmol) and PdCl2(dppf).CH2Cl2 adduct (1.75 g, 2.138 mmol) and Cs2CO3 (20.90 g, 64.1 mmol) and finally water (19.44 mL), and the mixture was stirred at 100° C. After stirring overnight the reaction was cooled to room temperature and 1N HCl (100 mL) was added. The layers were separated and the aqueous layer was extracted with EtOAc, washed with 1N HCl, dried over MgSO4, filtered and concentrated to provide the title compound, which was used in the next reaction without any further purification. MS (ESI−) m/z 399.2 (M−H).

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washwashed with 1N HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c89fafe4fc8b42f2b602653823b23ae2
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

반응 노트

불러오는 중…