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Potassium Phosphate, Tribasic → N-isobutyl-N-(3-methyl-5-(prop-1-en-2-yl)pyridin-2-yl)-4-((tetrahydro-2H-pyran yl)methoxy)benzenesulfonamide

HRID 594160
ノート
印刷プレビュー

反応式

HRID 594160 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH3:30])[C:5]([N:8]([CH2:26][CH:27]([CH3:29])[CH3:28])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19]C3CCOCC3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[N:6][CH:7]=1.[B-](F)(F)(F)[C:32]([CH3:34])=[CH2:33].[K+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1>[CH2:26]([N:8]([C:5]1[C:4]([CH3:30])=[CH:3][C:2]([C:2]([CH3:3])=[CH2:7])=[CH:7][N:6]=1)[S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH:15]2[CH2:14][CH2:34][CH2:32][CH2:33][O:18]2)=[CH:16][CH:17]=1)(=[O:11])=[O:10])[CH:27]([CH3:28])[CH3:29]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 23670158Potassium (prop-1-en-2-yl)trifluoroborateHCID 72194556N-(5-chloro-3-methylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

生成物 1

HCID 117926226N-isobutyl-N-(3-methyl-5-(prop-1-en-2-yl)pyridin-2-yl)-4-((tetrahydro-2H-pyran yl)methoxy)benzenesulfonamide収率 85%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
110 °C

実験手順

N-(5-chloro-3-methylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide (140 mg, 0.31 mmol), potassium trifluoro(prop-1-en-2-yl)borate (69 mg, 464 μmol) and Buchwald's Suzuki-Miyaura cross-coupling pre-catalyst (prepared according to ref. J. Am. Chem. Soc. 2010, 132, 14073) (5 mg, 6.18 μmol) were dissolved in anhydrous THF (1 mL). To this solution was added degassed potassium phosphate (0.5 M aqueous) (2 mL, 1.0 mmol) then the reaction vessel sealed and heated by microwaves to 110° C. for 30 minutes. The reaction was cooled, combined with a previous identical trial reaction on a smaller (0.06 mmol) scale and concentrated in vacuo. The crude product was then extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was passed through a hydrophobic frit, concentrated in vacuo, then purified by mass directed autoprep (formic acid modifier) to give the title compound 85% purity (87 mg). LCMS (2 min, formic) Rt 1.44 min, m/z (ES+) 459 (M+H).

後処理

  1. additionTo this solution was added
  2. customthe reaction vessel sealed
  3. temperatureThe reaction was cooled
  4. customcombined with a previous identical trial reaction on a smaller (0.06 mmol) scale
  5. concentrationconcentrated in vacuo
  6. extractionThe crude product was then extracted to the organic phase of an aqueous work up between ethyl acetate and water
  7. concentrationconcentrated in vacuo
  8. custompurified by mass

出典と根拠

ORDレコード
ord-ed6f3a36d13043c8b662c6419caeb025
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242972B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート