Azidotrimethylsilane → (5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol

HRID 931584ノート

反応式

HRID 931584 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:15]3([CH2:17][O:16]3)[C:14]3[CH:13]=[C:12]([Cl:18])[N:11]=[C:10]([F:19])[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[N:20]([Si](C)(C)C)=[N+:21]=[N-:22]>CN(C=O)C.CCOC(C)=O.O>[N:20]([C:15]1([CH2:17][OH:16])[C:14]2[CH:13]=[C:12]([Cl:18])[N:11]=[C:10]([F:19])[C:9]=2[O:8][C:5]2[C:4]1=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[N+:21]=[N-:22]

参加物

6

反応物 2

HCID 78378Azidotrimethylsilane2 回HCID 866583687-Bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,2'-oxirane]

生成物 1

HCID 86658369(5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol収率 99%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 7-bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,2′-oxirane] (23.5 g, 68.6 mmol) in DMF (600 mL) was added azidotrimethylsilane (54.6 mL, 412 mmol). The reaction mixture was stirred at RT for 6 hours. Additional azidotrimethylsilane (54.6 mL, 412 mmol) was added and the reaction was stirred at RT for 18 hours. The reaction mixture was diluted with EtOAc and water. The organic layer was separated, washed sequentially with a saturated aqueous LiCl solution and brine before drying over sodium sulfate. The solution was concentrated under reduced pressure to afford (5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol (26.12 g, 67.7 mmol, 99% yield).

後処理

  1. stirringthe reaction was stirred at RT for 18 hours
  2. customThe organic layer was separated
  3. washwashed sequentially with a saturated aqueous LiCl solution and brine
  4. dry with materialbefore drying over sodium sulfate
  5. concentrationThe solution was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-4227b21373d84fd486b45c43d4ed5e9b
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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