6-Benzyloxy-5-fluoro-1H-indole-2-carboxylic acid → 6-Benzyloxy-5-fluoro-1H-indole

HRID 1404080ノート

反応式

HRID 1404080 の反応式
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14](C(O)=O)[NH:15]2)=[CH:11][C:10]=1[F:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN1CCCC1=O.[Cu]>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][C:10]=1[F:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 1

HCID 583038746-Benzyloxy-5-fluoro-1H-indole-2-carboxylic acid

生成物 1

HCID 583039226-Benzyloxy-5-fluoro-1H-indole収率 60%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A mixture of compound 4-2 (2.58 g, 9.07 mmol) and copper (2.97 g, 45.1 mmol) in 80 mL of 1-methylpyrrolidin-2-one was heated at reflux overnight under nitrogen. After cooling to room temperature, the mixture was filtered through Celite and washed with EtOAc. The filtrate was partitioned between water and EtOAc (2×150 mL). The combined organic phase was washed with water and brine, and then dried over anhydrous Na2SO4. The black residue was purified by column chromatography (hexanes/EtOAc 2% to 12%) to give compound 4-3 (1.31 g, 60%) as a white solid. 1H NMR (CDCl3, 300 MHz) □ 5.16 (s, 2H), 6.94-6.98 (m, 1H), 6.96 (d, 1H, J=7.1), 7.10-7.14 (m, 1H), 7.29-7.42 (m, 4H), 7.44-7.50 (m, 2H), 8.01 (bs, 1H). APCI [M−1]: 240.

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight under nitrogen
  3. filtrationthe mixture was filtered through Celite
  4. washwashed with EtOAc
  5. customThe filtrate was partitioned between water and EtOAc (2×150 mL)
  6. washThe combined organic phase was washed with water and brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe black residue was purified by column chromatography (hexanes/EtOAc 2% to 12%)

出典と根拠

ORDレコード
ord-b837f7bdda17476cb3f3a2991098f4c4
出典データセット
uspto-grants-2014_12
特許番号
US08912220B2

反応ノート

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