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

HRID 387309

反応式

HRID 387309 の反応式
[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

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 593326735-Bromo-6-fluoro-3-(tetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 8759EDTA disodium salt触媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-482cd57ac7d64438b20f58dc92f7c8c8
出典データセット
uspto-grants-2013_02
特許番号
US08372875B2

関連ノート

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