Azidotrimethylsilane → ethyl 2-(5-azido-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)acetate

HRID 931599ノート

反応式

HRID 931599 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])O.[N:24]([Si](C)(C)C)=[N+:25]=[N-:26].C([O+]([B-](F)(F)F)CC)C>C1(C)C=CC=CC=1>[N:24]([C:5]1([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]2[CH:11]=[C:10]([Cl:12])[N:9]=[CH:8][C:7]=2[O:13][C:14]2[C:4]1=[CH:3][C:2]([Br:1])=[CH:16][CH:15]=2)=[N+:25]=[N-:26]

参加物

5

反応物 3

HCID 78378AzidotrimethylsilaneHCID 86658372ethyl 2-(7-bromo-3-chloro-5-hydroxy-5H-chromeno[2,3-c]pyridin-5-yl)acetateHCID 178467671HCID 178467671、化合物

生成物 1

HCID 86658373ethyl 2-(5-azido-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)acetate収率 99%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of ethyl 2-(7-bromo-3-chloro-5-hydroxy-5H-chromeno[2,3-c]pyridin-5-yl)acetate (20 g, 50.2 mmol) in toluene (300 ml) was added azidotrimethylsilane (19.93 ml, 151 mmol), followed by (diethyloxonio)trifluoroborate (12.72 ml, 100 mmol). The mixture was stirred overnight at RT. The reaction mixture was quenched with MeOH (200 mL) and diluted with EtOAc. The organic phase was separated, washed with saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to afford ethyl 2-(5-azido-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)acetate (21 g, 49.6 mmol, 99% yield).

後処理

  1. customThe reaction mixture was quenched with MeOH (200 mL)
  2. additiondiluted with EtOAc
  3. customThe organic phase was separated
  4. washwashed with saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-2bcf0a1cb5284491be6f1ad9a6c1dd41
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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