Dichloromethane → 5-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-6-fluoro-1H-indole-7-carboxamide

HRID 387309

반응식

HRID 387309 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([NH2:14])=[O:13])[C:10]=1[F:11])[NH:7][CH:6]=[C:5]2[CH:15]1[CH2:20][CH2:19]S[CH2:17][CH2:16]1.C([O-])(O)=O.[Na+].O[O:27][S:28]([O-:30])=O.[K+].C(Cl)Cl>COCCOC.O.C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC(O)=O.[Na+].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([NH2:14])=[O:13])[C:10]=1[F:11])[NH:7][CH:6]=[C:5]2[CH:15]1[CH2:20][CH2:19][S:28](=[O:30])(=[O:27])[CH2:17][CH2:16]1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 593326735-Bromo-6-fluoro-3-(tetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide2회

생성물 1

HCID 593326785-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-6-fluoro-1H-indole-7-carboxamide수율 19%

시약·촉매·용매 3

HCID 8759EDTA disodium salt촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매2회

실험 절차

An aqueous solution of 0.0004 M Na2EDTA (0.882 mL, 0.353 μmol) was added to a solution of 5-Bromo-6-fluoro-3-(tetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (45 mg, 0.126 mmol) in DME (3 mL). In a separate flask, NaHCO3 (106 mg, 1.260 mmol) was added to a solution of Oxone (232 mg, 0.378 mmol) in water (1 mL). This mixture was then added in 3 portions over 3 min to the DME solution of 5-Bromo-6-fluoro-3-(tetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide. The reaction was stirred at room temperature for 17 h. Water (2 mL) and DCM (3 mL) were added, the layers were separated, and the aqueous layer was extracted with DCM (3×2 mL). The combined organic layers were washed with saturated NaCl (1×2 mL), dried (Na2SO4), filtered, and concentrated under a stream of nitrogen at 50° C. The residue was dried under high vacuum, giving 9.2 mg (19%) of the title compound.

후처리

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with DCM (3×2 mL)
  3. washThe combined organic layers were washed with saturated NaCl (1×2 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under a stream of nitrogen at 50° C
  7. customThe residue was dried under high vacuum

출처 및 근거

ORD 기록
ord-482cd57ac7d64438b20f58dc92f7c8c8
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372875B2

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