Propargyl alcohol → 2-hydroxymethyl-1H-indole-5-carbaldehyde

HRID 591675ノート

反応式

HRID 591675 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=O)[CH3:11])=[C:5](I)[CH:4]=1)=[O:2].CN(C)C(N(C)C)=N.[CH2:22]([OH:25])C#C>CN(C=O)C.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>[OH:25][CH2:22][C:10]1[NH:9][C:6]2[C:7]([CH:11]=1)=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2

参加物

7

反応物 3

HCID 7859Propargyl alcoholHCID 664601,1,3,3-TetramethylguanidineHCID 229919464-Acetamido-3-iodobenzaldehyde

生成物 1

HCID 866620272-hydroxymethyl-1H-indole-5-carbaldehyde

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 6228Dimethylformamide溶媒

実験手順

To a degassed solution of N-(4-formyl-2-iodo-phenyl)-acetamide (0.760 g, 2.63 mmol) in anhydrous DMF (20 mL) were added bis(triphenylphosphine)palladium(II) dichloride (90 mg, 0.13 mmol), copper (I) iodide (0.03 g, 0.13 mmol), 1,1,3,3-tetramethyl guanidine (1.51 g, 13.1 mmol), and propargyl alcohol (0.210 g, 3.68 mmol). The reaction mixture was stirred at room temperature for 2 hours and then at 80° C. for 24 hours under nitrogen. Solvent was evaporated under reduced pressure. Water (100 mL) was added and the mixture was extracted with ethyl acetate (200 mL). The organic phase was backwashed with water (2×100 mL), brine (100 mL), and dried over anhydrous Na2SO4. Solvent was evaporated and crude compound was purified by the Simpliflash system (60% ethyl acetate in hexanes as eluent) to give 2-hydroxymethyl-1H-indole-5-carbaldehyde as a pale yellow solid. Yield: 0.10 g (22%).

後処理

  1. waitat 80° C. for 24 hours under nitrogen
  2. customSolvent was evaporated under reduced pressure
  3. additionWater (100 mL) was added
  4. extractionthe mixture was extracted with ethyl acetate (200 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customSolvent was evaporated
  7. customcrude compound was purified by the Simpliflash system (60% ethyl acetate in hexanes as eluent)

出典と根拠

ORDレコード
ord-693604ae779f4ca482f4ba8636b6d6b6
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

反応ノート

読み込み中…