Triethylamine → (S)-Ethyl [N-({5-[(3-hydroxyphenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate

HRID 1099659

反応式

HRID 1099659 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]([N:10]=[S:11]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[O:9])[CH:5]=[N:6][CH:7]=1.[OH:25][C:26]1[CH:27]=[C:28]([C:32]#[CH:33])[CH:29]=[CH:30][CH:31]=1.C(N(CC)CC)C>CN(C=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:25][C:26]1[CH:27]=[C:28]([C:32]#[C:33][C:2]2[CH:3]=[C:4]([C:8]([N:10]=[S@:11]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])=[O:9])[CH:5]=[N:6][CH:7]=2)[CH:29]=[CH:30][CH:31]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 139144m-EthynylphenolHCID 76585243ethyl {N-[(5-bromopyridin-3-yl)carbonyl]-S-phenylsulfonimidoyl}acetate

生成物 1

HCID 24954917(S)-Ethyl [N-({5-[(3-hydroxyphenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate収率 94.3%

試薬・触媒・溶媒 2

HCID 11776Triphenylphosphine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A solution ethyl {N-[(5-bromopyridin-3-yl)carbonyl]-S-phenylsulfonimidoyl}acetate (216 mg, 0.52 mmol) and 3-hydroxyphenylacetylene (0.052 mL, 0.79 mmol) in anhydrous DMF (3 mL) was treated with triethylamine (0.22 mL, 1.58 mmol). The reaction mixture was degassed (alternating vacuum and argon) and PdCl2(Ph3P)2 (36.9 mg, 0.052 mmol) and triphenylphosphine (3.4 mg, 0.013 mmol) were added. The reaction mixture was degassed (alternating vacuum and argon) and placed under an atmosphere of 1:3 Argon/hydrogen atmosphere. Copper(1+) iodide was added and the reaction mixture was heated at 60° C. for 50 min. The brown reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc. The organic layer was collected and washed further with saturated aqueous NaHCO3 (1×), brine (1×), and dried over anhydrous Na2SO4. The residue was purified by chromatography (silica gel, 50:1 CHCl3:MeOH). The product containing fractions were concentrated to give the title compound as a light yellow solid (220 mg, 94%).

後処理

  1. additionwere added
  2. customThe reaction mixture was degassed (alternating vacuum and argon)
  3. additionCopper(1+) iodide was added
  4. customThe brown reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc
  5. customThe organic layer was collected
  6. washwashed further with saturated aqueous NaHCO3 (1×), brine (1×)
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe residue was purified by chromatography (silica gel, 50:1 CHCl3:MeOH)
  9. additionThe product containing fractions
  10. concentrationwere concentrated

出典と根拠

ORDレコード
ord-6e6a6fd1f26b404b96e6248ed25dcd75
出典データセット
uspto-grants-2012_03
特許番号
US08143410B2

関連ノート

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