Triethylamine → (E)-2-(2-Amino-5-chloro-3-pyridinyl)-N-methyl-1-ethenesulphonamide

HRID 1370588ノート

反応式

HRID 1370588 の反応式
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:10][NH:11][S:12]([CH:15]=[CH2:16])(=[O:14])=[O:13].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:9][C:3]1[C:2](/[CH:16]=[CH:15]/[S:12]([NH:11][CH3:10])(=[O:14])=[O:13])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 27639713-Bromo-5-chloropyridin-2-amineHCID 21895383N-Methylethenesulfonamide

生成物 1

HCID 18752899(E)-2-(2-Amino-5-chloro-3-pyridinyl)-N-methyl-1-ethenesulphonamide収率 25%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-bromo-5-chloro-2-pyridinamine (414 mg, 2 mmol), N-methyl ethene sulphonamide (266 mg, 2.2 mmol) and triethylamine (555 μl, 4 mmol), palladium acetate (18 mg, 0.08 mmol) and tri-o-tolylphosphine (50 mg, 0.16 mmol) in DMF (0.5 ml) in a Teflon™ pressure vessel was microwaved for 30 sec (full power), allowed to cool to RT and irradiated for a further 30 sec. After allowing to cool, the reaction mixture was diluted with water, extracted with EtOAc and the organic phase washed with saturated brine, dried over MgSO4, and concentrated to a brown semi-solid. Purification by column chromatography on silica gel eluting with methylene chloride—methanol (95:5), and then crystallisation from methanol gave the title compound (130 mg, 0.5 mmol):

後処理

  1. customwas microwaved for 30 sec (full power)
  2. customirradiated for a further 30 sec
  3. temperatureto cool
  4. extractionextracted with EtOAc
  5. washthe organic phase washed with saturated brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to a brown semi-solid
  8. customPurification by column chromatography on silica gel eluting with methylene chloride—methanol (95:5)
  9. customcrystallisation from methanol

出典と根拠

ORDレコード
ord-ddeef1df2bc9424bbcff886ed4886177
出典データセット
uspto-grants-2003_06
特許番号
US06583162B1

反応ノート

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