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

HRID 1670254ノート

反応式

HRID 1670254 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-20510ded60b14a9dbb04e3931f1e1ad6
出典データセット
uspto-grants-2011_08
特許番号
US07989477B2

反応ノート

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