Citric Acid → HCID 178497462, 화합물

HRID 1862095노트

반응식

HRID 1862095 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][NH:19]3)=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][O:11][CH3:12].[I:22]I.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.OS([O-])=O.[Na+]>O1CCOCC1.[OH-].[Na+].II.C(OCC)(=O)C.CCCCCC>[I:22][C:17]1[C:16]2[C:20](=[CH:21][C:13]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH2:10][O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:14][CH:15]=2)[NH:19][N:18]=1

참가 물질

9

반응물 4

HCID 311Citric AcidHCID 807IodineHCID 218774636-(3-methoxy-4-methoxymethoxy-phenyl)-1H-indazoleHCID 23665763Sodium Bisulfite

생성물 1

HCID 178497462HCID 178497462, 화합물수율 78%

시약·촉매·용매 4

HCID 807Iodine촉매HCID 14798Sodium Hydroxide용매HCID 312751,4-Dioxane용매HCID 21226206Ethyl acetate hexane용매

실험 절차

In a 100-mL round-bottom flask under argon, 6-(3-methoxy-4-methoxymethoxy-phenyl)-1H-indazole (1.19 g, 4.18 mmol, 1 equiv) was dissolved in dioxane (25 mL) and 3N NaOH (14 mL). This mixture was treated with iodine (1.17 g, 14.60 mmol, 1.10 equiv) added in ˜5 portions (˜10 min). Several (˜4) additional portions of iodine (50 mg each) were added until the reaction was complete as visualized by TLC (3:7 ethyl acetate/hexane). The mixture was acidified with 20% citric acid (25 mL) and 5% NaHSO3 (20 mL) was added. The mixture was partitioned between ethyl acetate (150 mL) and water (100 mL). The organic material was washed with saturated sodium bicarbonate (80 mL) and brine (50 mL) and were dried over sodium sulfate and concentrated under reduced pressure. Purification by crystallization from ethyl acetate (3 mL) then hexane (7 mL) gave pure 3-iodo-6-(3-methoxy-4-methoxymethoxy-phenyl)-1H-indazole as a solid (1.33 g, 78%): 1H NMR (CDCl3) δ 10.48 (bs, 1H), 7.62 (s, 1H), 7.57 (d, 1H, J=8.5 Hz), 7.47 (dd, 1H, J=1.3, 8.5 Hz), 7.18 (m, 3H), 5.29 (s, 2H), 3.99 (s, 3H), 3.55 (s, 3H).

후처리

  1. additionadded in ˜5 portions (˜10 min)
  2. additionwas added
  3. customThe mixture was partitioned between ethyl acetate (150 mL) and water (100 mL)
  4. washThe organic material was washed with saturated sodium bicarbonate (80 mL) and brine (50 mL)
  5. dry with materialwere dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. customby crystallization from ethyl acetate (3 mL)

출처 및 근거

ORD 기록
ord-4101f6d66cee423e80759d818f58e79f
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06534524B1

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