Cesium carbonate → Ethyl 3-(5-cyano-1H-indazol-1-yl)propanoate

HRID 2189778ノート

反応式

HRID 2189778 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C)C=O.CCOC(C)=O>[C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[N:1]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:2]=[CH:3]2)#[N:11]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 68320Ethyl 3-bromopropionateHCID 111263841H-Indazole-5-carbonitrile

生成物 1

HCID 59316705Ethyl 3-(5-cyano-1H-indazol-1-yl)propanoate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

1H-indazole-5-carbonitrile (D1) (3.5 g, 24.45 mmol) was dissolved in N,N-dimethylformamide (60 ml). cesium carbonate (15.93 g, 48.9 mmol) and ethyl 3-bromopropanoate (4.68 ml, 36.7 mmol) were added. The mixture was heated at 80° C. for 4 hours. Diluted with EtOAc and washed with water (3×40 ml), dried over MgSO4 and evaporated. The mixture was purified by flash chromatography, eluting EtOAc/iso-Hexane 10-30% then 10-20% to give (3.682 g) for the first isomer (yellow oil) and (1.509 g) for the second isomer (pink solid). Analysis of the first isomer by 1H nmr indicated that is was the 1-isomer contaminated with the 2-isomer (ca. 20%) δH (d6-DMSO, 400 MHz) 1.05 (3H, t), 2.95 (2H, t), 3.97 (2H, q), 4.69 (2H, t), 7.74 (1H, dd), 7.92 (1H, dt), 8.28 (1H, d), 8.38 (1H, dd). MS (ES+): C13H13N3O2 requires 243; found (MH+) 244.

後処理

  1. washwashed with water (3×40 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe mixture was purified by flash chromatography
  5. washeluting EtOAc/iso-Hexane 10-30%
  6. custom10-20% to give (3.682 g) for the first isomer (yellow oil) and (1.509 g) for the second isomer (pink solid)

出典と根拠

ORDレコード
ord-500a158a08024a3bb41f610e48df533d
出典データセット
uspto-grants-2012_12
特許番号
US08324254B2

反応ノート

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