Tetrahydrofuran → 2-[3-(2-methoxy-ethoxy)-phenyl]-5-nitro-1H-pyrrolo[2,3-b]pyridine

HRID 502797노트

반응식

HRID 502797 반응식
CC(C)([O-])C.[K+].[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:18]#[C:19][C:20]2[C:21]([NH2:29])=[N:22][CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=2)[CH:15]=[CH:16][CH:17]=1.O1CCCC1>CN(C)C=O>[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:18]2[NH:29][C:21]3=[N:22][CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=[C:20]3[CH:19]=2)[CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 684671423-[3-(2-Methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamine

생성물 1

HCID 684671552-[3-(2-methoxy-ethoxy)-phenyl]-5-nitro-1H-pyrrolo[2,3-b]pyridine수율 83%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

Potassium tert-butoxide (1.18 g, 10.5 mmol) was added to a solution of 3-[3-(2-methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamine (1.57 g, 5 mmol) in a 2:1 mixture of tetrahydrofuran and dimethylformamide (75 mL). The mixture was heated at 70° C. for 16 hours then the tetrahydrofuran was removed in vacuo. The mixture was poured onto a pad of silica and eluted with ethyl acetate then 10% methanol in ethyl acetate. The organics were concentrated in vacuo to 5% of their original volume and water (30 mL) was added. The resultant orange solid was filtered and dried to afford 2-[3-(2-methoxy-ethoxy)-phenyl]-5-nitro-1H-pyrrolo[2,3-b]pyridine (1.3 g, 83%).

후처리

  1. customthe tetrahydrofuran was removed in vacuo
  2. additionThe mixture was poured onto a pad of silica
  3. washeluted with ethyl acetate
  4. concentrationThe organics were concentrated in vacuo to 5% of their original volume and water (30 mL)
  5. additionwas added
  6. filtrationThe resultant orange solid was filtered
  7. customdried

출처 및 근거

ORD 기록
ord-9e3e236b766d431c827e8ba480dd0045
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776878B2

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