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

HRID 455596ノート

反応式

HRID 455596 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 99.3%

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 (38.5 g, 97 mmol) in toluene (400 ml) was added azidotrimethylsilane (38.4 ml, 290 mmol) followed by (diethyloxonio)trifluoroborate (24.48 ml, 193 mmol) under an atmosphere of nitrogen. The reaction mixture was stirred at RT for 16 hours. 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 (40.82 g) which was used in the next step without further purification.

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-1bf6fa0712d54467a28cec5671fe51a3
出典データセット
uspto-grants-2013_07
特許番号
US08497264B2

反応ノート

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