Hydrochloric Acid → 5-[1-(4-Fluoro-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol

HRID 1633634ノート

反応式

HRID 1633634 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[CH2:25]([OH:30])[CH2:26][CH2:27][C:28]#[CH:29].Cl>N1CCCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu](I)I>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:29]#[C:28][CH2:27][CH2:26][CH2:25][OH:30])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 793464-Pentyn-1-ol2 回HCID 86585583Trifluoro-methanesulfonic acid 1-(4-fluoro-phenyl)-1H-indol-5-yl ester

生成物 1

HCID 186795225-[1-(4-Fluoro-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol収率 96.4%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8082Piperidine溶媒

実験手順

To 2.25 g (6.25 mmol) Trifluoro-methanesulfonic acid 1-(4-fluoro-phenyl)-1H-indol-5-yl ester in 12.5 ml piperidine were added 360 mg (0.31 mmol) tetrakis(triphenylphosphine)-palladium followed by 60.0 mg (0.31 mmol) copper iodide. The solution was evaporated and flushed with argon prior to the addition of 450 μl (4.95 mmol) 4-pentynol at 80° C. over a period of 45 min. Further 0.45 ml (4.95 mmol) 4-pentynol were added and the solution was stirred for 2 h. The mixture was added to ice water, acidified with 2M HCl and extracted with ether. The combined organic phases were washed with water and dried over Na2SO4. Purification by column chromatography with CH2Cl2/MeOH 19:1 yielded 1.4 g (76%) 5-[1-(4-Fluoro-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol as light yellow waxy solid, MS: 293 (M).

後処理

  1. customThe solution was evaporated
  2. customflushed with argon
  3. extractionextracted with ether
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4
  6. customPurification by column chromatography with CH2Cl2/MeOH 19:1

出典と根拠

ORDレコード
ord-67979a05947a4dcb877c09d871428e19
出典データセット
uspto-grants-2003_01
特許番号
US06503907B2

反応ノート

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