홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Ammonium Chloride → {2-Fluoro-3-[3-(pyridin-4-yloxy)azetidin-1-yl]phenyl}methanol

HRID 1021238
노트
인쇄 미리보기

반응식

HRID 1021238 반응식
Br[C:2]1[C:3]([F:17])=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][Si](C(C)(C)C)(C)C.[NH:18]1[CH2:21][CH:20]([O:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH2:19]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.[Cl-].[NH4+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)(Cl)Cl.C1COCC1.CCOC(C)=O.C1(C)C=CC=CC=1>[F:17][C:3]1[C:2]([N:18]2[CH2:21][CH:20]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[CH2:19]2)=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][OH:6]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

12

반응물 6

HCID 25517Ammonium ChlorideHCID 634876Binap, (A+-)-HCID 11078149TBAF tetrahydrofuranHCID 23676156Sodium t-butoxideHCID 509882824-(Azetidin-3-yloxy)pyridineHCID 86686195((3-Bromo-2-fluorobenzyl)oxy)(tert-butyl)dimethylsilane

생성물 1

HCID 68309778
{2-Fluoro-3-[3-(pyridin-4-yloxy)azetidin-1-yl]phenyl}methanol
수율 68.4%

시약·촉매·용매 5

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

Under argon atmosphere, [(3-bromo-2-fluorobenzyl)oxy](tert-butyl)dimethylsilane (800 mg) and 4-(azetidin-3-yloxy)pyridine (268 mg) were mixed with toluene (6 ml), and Pd2(dba)3 (80 mg), BINAP (160 mg), and sodium tert-butoxide (300 mg) were added thereto, followed by stirring at 90° C. for 3 hours. The reaction mixture was cooled to room temperature, and EtOAc was added thereto, followed by carrying out filtration using Celite as a filtration adjuvant. The filtrate was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/EtOAc). The purified product thus obtained was mixed with THF (6 ml), and a 1 M TBAF/THF solution (3 ml) was added thereto, followed by stirring at room temperature for 1 hour. To the reaction mixture were added a saturated aqueous ammonium chloride solution and CHCl3, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain {2-fluoro-3-[3-(pyridin-4-yloxy)azetidin-1-yl]phenyl}methanol (335 mg).

후처리

  1. additionwere added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/EtOAc)
  6. customThe purified product thus obtained
  7. stirringby stirring at room temperature for 1 hour
  8. dry with materialthe organic layer was dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-669c096e3dfb4e2b9a740228430ce9f3
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08716470B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트