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

HRID 931614ノート

反応式

HRID 931614 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e6a4f565334949c4bf4de6dcb60784cc
出典データセット
uspto-grants-2016_03
特許番号
US09296759B2

反応ノート

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