Water → HCID 86712654, 화합물

HRID 1778991노트

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HRID 1778991 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 86712654HCID 86712654, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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]+.

후처리

  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.)

출처 및 근거

ORD 기록
ord-267e14ca25ae4e278b5b6cba922ba8b3
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266864B2

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