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

HRID 1404080노트

반응식

HRID 1404080 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

HCID 583039226-Benzyloxy-5-fluoro-1H-indole수율 60%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-b837f7bdda17476cb3f3a2991098f4c4
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912220B2

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