Trifluoroacetic acid → 5-Allyloxy-7-(4-fluoro-benzyl)-9-hydroxy-pyrrolo[3,4-g]quinoline-6,8-dione

HRID 853620노트

반응식

HRID 853620 반응식
[CH2:1]([O:4][C:5]1[C:14]2[C:15](=[O:27])[N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:17](=[O:18])[C:13]=2[C:12]([O:28]COC)=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)[CH:2]=[CH2:3].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:4][C:5]1[C:14]2[C:15](=[O:27])[N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:17](=[O:18])[C:13]=2[C:12]([OH:28])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)[CH:2]=[CH2:3]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acid2회HCID 589289585-Allyloxy-7-(4-fluoro-benzyl)-9-methoxymethoxy-pyrrolo[3,4-g]quinoline-6,8-dione

생성물 1

HCID 104747705-Allyloxy-7-(4-fluoro-benzyl)-9-hydroxy-pyrrolo[3,4-g]quinoline-6,8-dione수율 44%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-Allyloxy-7-(4-fluoro-benzyl)-9-methoxymethoxy-pyrrolo[3,4-g]quinoline-6,8-dione 10 was dissolved in 1 mL dichloromethane. Ten equivalents of trifluoroacetic acid was added and the mixture was stirred at room temperature. After one hour another 10 equivalents of trifluoroacetic acid was added. The mixture was then stirred overnight, concentrated in vacuo, and azeotroped with toluene (2×), to give crude 11 which was triturated with 2 mL of 1:1 diethylether/hexane two times to give allyl ether 11 (0.0025 g, 0.0066 mmol, 44%). 1H NMR (CDCl3) δ 9.0 (s, 1H), 8.7 (d, 1H), 7.7 (m, 1H), 7.5 (m, 2H), 7.0 (t, 2H), 6.1 (m, 1H), 5.4 (d, 1H), 5.3 (d, 1H), 5.1 (d, 2H), 4.8 (s, 2H). MS: 379 (M+1).

후처리

  1. stirringThe mixture was then stirred overnight
  2. concentrationconcentrated in vacuo
  3. customazeotroped with toluene (2×)
  4. customto give crude 11 which
  5. customwas triturated with 2 mL of 1:1 diethylether/hexane two times

출처 및 근거

ORD 기록
ord-d64fa2e0a1bc47a1a3fee72a0bc884ed
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253180B2

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