Water → tert-Butyl 4-(2-(4-(4-amino-2-fluorophenoxy)pyridin-3-yl)ethynyl)cyclohex-3-enylcarbamate

HRID 2374001노트

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HRID 2374001 반응식
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]#[C:12][C:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:15][CH:14]=1.[NH4+].[Cl-].CN(C=O)C.O>[Fe].CCO>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[C:11]#[C:12][C:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:15][CH:14]=2)=[C:2]([F:1])[CH:30]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 59853035Tert-butyl 4-(2-(4-(2-fluoro-4-nitrophenoxy)pyridin-3-yl)ethynyl)cyclohex-3-enylcarbamate

생성물 1

HCID 59853058tert-Butyl 4-(2-(4-(4-amino-2-fluorophenoxy)pyridin-3-yl)ethynyl)cyclohex-3-enylcarbamate수율 103.3%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

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온도
100 °C

실험 절차

A mixture of tert-butyl 4-(2-(4-(2-fluoro-4-nitrophenoxy)pyridin-3-yl)ethynyl)cyclohex-3-enylcarbamate (110 mg, 0.24 mmol), iron powder, ˜325 mesh (150 mg, 2.7 mmol), NH4Cl (280 mg, 5.3 mmol), DMF (1 mL), H2O (1 mL) and EtOH (1 mL) was heated at 100° C. for 30 minutes. The mixture was filtered through a pad of Celite® using DMF to wash the filter cake and the filtrate made basic to pH 8 with saturated aq. NaHCO3 solution. The mixture was extracted twice with EtOAc and dried (MgSO4) and concentrated in vacuo to give the title compound (105 mg) which was used without any further purification. MS(ESI+): m/z 424.27 (M+H)+.

후처리

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. washto wash the filter cake
  3. extractionThe mixture was extracted twice with EtOAc
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-713c083af00b40bab4387ee91d9922ae
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07459562B2

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