Azidotrimethylsilane → ethyl 2-(9-azido-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)acetate

HRID 931605ノート

反応式

HRID 931605 の反応式
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:25])=[CH:9][C:10]([O:23][CH3:24])=[CH:11][C:12]=3[C:13]2([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])O)=[CH:4][CH:3]=1.[N:26]([Si](C)(C)C)=[N+:27]=[N-:28].C([O+]([B-](F)(F)F)CC)C>C1(C)C=CC=CC=1>[N:26]([C:13]1([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12]2[CH:11]=[C:10]([O:23][CH3:24])[CH:9]=[C:8]([F:25])[C:7]=2[O:6][C:5]2[C:14]1=[CH:15][C:2]([Br:1])=[CH:3][CH:4]=2)=[N+:27]=[N-:28]

参加物

5

反応物 3

HCID 78378AzidotrimethylsilaneHCID 67383096ethyl 2-(7-bromo-4-fluoro-9-hydroxy-2-methoxy-9H-xanthen-9-yl)acetateHCID 178467671HCID 178467671、化合物

生成物 1

HCID 86658377ethyl 2-(9-azido-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)acetate収率 94.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

To a solution of ethyl 2-(7-bromo-4-fluoro-9-hydroxy-2-methoxy-9H-xanthen-9-yl)acetate (1.0 g, 2.432 mmol) in toluene (25 ml) was added azidotrimethylsilane (0.560 g, 4.86 mmol). The solution was cooled to 0° C. and (diethyloxonio)trifluoroborate (0.308 ml, 2.432 mmol) was added drop wise. The mixture was stirred overnight at RT. The solution was quenched with MeOH (10 ml) and diluted with EtOAc. The organic phase was separated, washed with saturated aqueous sodium bicarbonate solution and brine, and then concentrated to afford crude ethyl 2-(9-azido-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)acetate (1 g, 2.292 mmol, 94% yield).

後処理

  1. customThe solution was quenched with MeOH (10 ml)
  2. additiondiluted with EtOAc
  3. customThe organic phase was separated
  4. washwashed with saturated aqueous sodium bicarbonate solution and brine
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-eeb16aaac29546de96e31fb767174315
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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