HCID 9967388, 화합물 → 3-(5'-Hydroxymethyl-2'-furyl)-1-benzylindazole

HRID 1743354노트

반응식

HRID 1743354 반응식
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22](OC)=[O:23])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([CH2:22][OH:23])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

3

반응물 1

HCID 9967388HCID 9967388, 화합물

생성물 1

HCID 57123-(5'-Hydroxymethyl-2'-furyl)-1-benzylindazole수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 1-benzyl-3-(5-methoxycarbonyl-2-furyl)-1H-indazole in THF (150 mL) was added dropwise to a suspension of CaBH4.2THF (3.9 g, 18.23 mmol) in THF (150 mL) at room temperature. The resultant mixture was heated to reflux for 15 h. The reaction mixture was allowed to cool, then poured slowly onto brine. The layers were separated and the aqueous layer was extracted three times with ether. The combined organic material was dried (MgSO4) and concentrated under reduced pressure. The crude product was chromatographed on silica (30–40% EtOAc/cyclohexane) and then recrystallised (ethanol/H2O) to give the product as fine cream needles (1.56 g, 86%): mp 112–112.5° C. (lit. mp 108–109° C.); MS (EI) M+ 304; 1H-NMR (CDCl3) 4.76 (s, 2H), 5.68 (s, 2H), 6.50 (d, 1H, J=3.3 Hz), 6.90 (d, 1H, J=3.3 Hz), 7.21–7.40 (m, 8H), 8.08 (d, 1H, J=8.5 Hz); 13C-NMR (CDCl3) 54.12, 58.53, 108.87, 110.57, 110.59, 122.25, 122.38,122.50, 127.83, 128.00(2C), 128.72, 129.68(2C), 137.14, 137.53, 141.45, 149.52, 154.88; Anal. (C19H16N2O2) C, calcd 74.98; found 74.80, H, calcd 5.30; found 5.28, N, calcd 9.20; found 9.15.

후처리

  1. customat room temperature
  2. temperatureto reflux for 15 h
  3. temperatureto cool
  4. additionpoured slowly onto brine
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted three times with ether
  7. dry with materialThe combined organic material was dried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was chromatographed on silica (30–40% EtOAc/cyclohexane)
  10. customrecrystallised (ethanol/H2O)

출처 및 근거

ORD 기록
ord-ab81dcb47f4f44bd920ef90a943a28bb
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07009056B2

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