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Sodium bis(trimethylsilyl)amide → 6-Bromo-3,3-difluoro-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one

HRID 2209286
ノート
印刷プレビュー

反応式

HRID 2209286 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([F:13])([F:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30]>CN(C=O)C.C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([F:13])([F:12])[C:7](=[O:11])[N:8]2[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 722182316-Bromo-3,3-difluoroindolin-2-one

生成物 1

HCID 1234084286-Bromo-3,3-difluoro-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

Into the solution of 6-bromo-3,3-difluoroindolin-2-one in DMF (5 mL), was added 1M of NaHMDS solution in THF (1.6 mL), after 30 min., (2-(chloromethoxy)ethyl)trimethylsilane (269 mg) was added. After being stirred at rt for 4 h, the reaction mixture was extracted with ethyl acetate and washed with brine, dried and the solvent was removed, the residue was purified by silica gel chromatography to provide 0.46 g of 6-bromo-3,3-difluoro-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one 7.35. 1H NMR (400 MHz, Chloroform-d) δ 7.43 (s, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.33 (d, J=8.1 Hz, 1H), 5.12 (s, 2H), 3.58 (m, 2H), 1.21 (m, 2H), 0.00 (s, 9H).

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. customdried
  4. customthe solvent was removed
  5. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-1de3a3149b704a3b981a834be4a6fa62
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09376441B2

反応ノート

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