Aluminium lithium hydride → 2-(5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)ethanol

HRID 931614노트

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HRID 931614 반응식
[N:1]([C:4]1([CH2:20][C:21](OC(C)(C)C)=[O:22])[C:17]2[C:12](=[N:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[O:11][C:10]2[C:5]1=[CH:6][C:7]([I:19])=[CH:8][CH:9]=2)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][C:4]1([CH2:20][CH2:21][OH:22])[C:17]2[C:12](=[N:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[O:11][C:10]2[C:5]1=[CH:6][C:7]([I:19])=[CH:8][CH:9]=2

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 86658379tert-butyl 2-(5-azido-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate

생성물 1

HCID 673828752-(5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)ethanol수율 37.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

In a 1-L flask, the tert-butyl 2-(5-azido-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate (7.27 g, 13.38 mmol) was suspended in THF (100 mL) and the suspension was cooled to 0° C. A THF solution of LAH (1 M, 20.08 mL, 20.08 mmol) was added. After 30 min, the reaction mixture was quenched with careful addition of water (0.75 mL), 4 M aqueous NaOH (2.2 mL), and water (0.75 mL). The mixture was filtered through Celite, rinsing with THF (60 mL), then with EtOAc (150 mL). The combined filtrate was concentrated. The residue was purified through silica gel (400 mL) which had been deactivated with Et3N (40 mL), using 100:100:1 EtOAc-hexane-Et3N, to afford 2-(5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)ethanol (2.24 g).

후처리

  1. customthe reaction mixture was quenched with careful addition of water (0.75 mL), 4 M aqueous NaOH (2.2 mL), and water (0.75 mL)
  2. filtrationThe mixture was filtered through Celite
  3. washrinsing with THF (60 mL)
  4. concentrationThe combined filtrate was concentrated
  5. customThe residue was purified through silica gel (400 mL) which

출처 및 근거

ORD 기록
ord-e6a4f565334949c4bf4de6dcb60784cc
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296759B2

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