Triethylamine → (S)-5-({3-[(2-methylbenzoyl)amino]phenyl}ethynyl)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

HRID 1099645ノート

反応式

HRID 1099645 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:6]=[CH:7][CH:8]=1)#[CH:2].Br[C:20]1[CH:21]=[N:22][CH:23]=[C:24]([CH:37]=1)[C:25]([N:27]=[S@@:28]([CH3:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].CCN(CC)CC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CCOC(C)=O>[CH3:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]([NH:9][C:5]1[CH:4]=[C:3]([C:1]#[C:2][C:20]2[CH:21]=[N:22][CH:23]=[C:24]([CH:37]=2)[C:25]([N:27]=[S@@:28]([CH3:36])(=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH:8]=[CH:7][CH:6]=1)=[O:18]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 24676237N-(3-ethynylphenyl)-2-methylbenzamideHCID 86629466(S)-5-bromo-N-[methyl(oxido)phenyl--sulfanylidene]nicotinamide

生成物 1

HCID 24953840(S)-5-({3-[(2-methylbenzoyl)amino]phenyl}ethynyl)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide収率 83.1%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

In a 4 mL vial, N-(3-ethynylphenyl)-2-methylbenzamide (0.104 g, 0.443 mmol) and (S)-5-bromo-N-[methyl(oxo)phenyl-λ6-sulfanylidene]nicotinamide (0.100 g, 0.295 mmol) were added and dissolved into EtOAc (2 mL) The mixture was then degassed for ˜20 min after which NEt3 (0.141 mL, 1.035 mmol) was added followed by Pd(PPh3)2Cl2 (21.0 mg, 0.030 mmol) and CuI (2.9 mg, 0.016 mmol). The reaction mixture was allowed to stir at 50° C. for 4 hours after which the reaction mixture was partitioned between EtOAc (4 mL) and water (4 mL). The organic extracts were combined, dried over anhydrous Na2SO4 and concentrated. The residue as purified by chromatography (silica gel, gradient elution 25% EtOAc/Hexanes EtOAc). The product containing fractions were concentrated to give the title compound as a solid (121 mg, 83%).

後処理

  1. additionwas added
  2. customwas partitioned between EtOAc (4 mL) and water (4 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue as purified by chromatography (silica gel, gradient elution 25% EtOAc/Hexanes EtOAc)
  6. additionThe product containing fractions
  7. concentrationwere concentrated

出典と根拠

ORDレコード
ord-47a4493431d845c69cfaa9a1d8f2b207
出典データセット
uspto-grants-2012_03
特許番号
US08143410B2

反応ノート

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