Water → HCID 86712654、化合物

HRID 1778991ノート

反応式

HRID 1778991 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]#[C:13][Si](C)(C)C)=[C:6]([CH2:8][C:9]([NH2:11])=[O:10])[CH:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C(Cl)Cl>[C:12]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[CH2:8][C:9]([NH2:11])=[O:10])#[CH:13]

参加物

5

反応物 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 867126522-(5-Fluoro-2-((trimethylsilyl)ethynyl)phenyl)acetamide

生成物 1

HCID 86712654HCID 86712654、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-(5-fluoro-2-((trimethylsilyl)ethynyl)phenyl)acetamide (A34) (0.239 g, 0.958 mmol) in DCM (10 mL) at 0° C. was added TBAF (1.0 M in THF; 1.44 mL, 1.44 mmol). The resulting mixture was stirred at 0° C. for 10 minutes, then poured into water (50 mL). The organic phase was separated and the aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were washed with brine, dried (MgSO4) and the volatiles removed in vacuo. The residue was adsorbed onto silica gel then purified by column chromatography (Biotage Isolera, SiO2, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A35 as a white solid (0.114 g, 67%); 1H NMR (400 MHz, d6-DMSO) δ 7.50 (dd, J=8.6, 5.9 Hz, 1H), 7.44 (s, 1H), 7.17 (dd, J=10.0, 2.7 Hz, 1H), 7.10 (td, J=8.6, 2.8 Hz, 1H), 6.99 (s, 1H), 4.32 (s, 1H), 3.61 (s, 2H). LCMS-A: rt 4.843 min; m/z 178 [M+H]+.

後処理

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted with DCM (2×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe volatiles removed in vacuo
  6. customthen purified by column chromatography (Biotage Isolera, SiO2, 0-100% EtOAc in petroleum benzine 40-60° C.)

出典と根拠

ORDレコード
ord-267e14ca25ae4e278b5b6cba922ba8b3
出典データセット
uspto-grants-2016_02
特許番号
US09266864B2

反応ノート

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