Ethyl bromoacetate → Ethyl (3-isobutyryl-6-methoxy-1H-indazol-1-yl)acetate

HRID 229458ノート

反応式

HRID 229458 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[N:8][NH:9]2)=[CH:5][CH:4]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].CCOC(C)=O>CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>[C:12]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:9]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:8]=1)(=[O:16])[CH:13]([CH3:14])[CH3:15]

参加物

6

反応物 3

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 588238251-(6-methoxy-1H-indazol-3-yl)-2-methylpropan-1-one

生成物 1

HCID 86618180Ethyl (3-isobutyryl-6-methoxy-1H-indazol-1-yl)acetate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 10796Cesium carbonate溶媒

実験手順

Dissolve 5.456 g of 1-(6-methoxy-1H-indazol-3-yl)-2-methylpropan-1-one in 100 mL anhydrous DMF. Weigh in 8.96 g cesium carbonate followed by 4.593 g ethyl bromoacetate. The resulting mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. Partition the residue between EtOAc and water. Extract the aqueous layer with EtOAc several times. The combined organic extract was washed with water (3×) and saturated brine, dried over anhydrous Na2SO4, and evaporated to give the crude product. The title compound was obtained by recrystallization from 40 mL 4:1 hexanes and EtOAc. 1H NMR (CDCl3, 500 MHz) δ 8.26 (d, 8.9 Hz, 1H), 7.00 (dd, 2.1 & 9.0 Hz, 1H), 6.685 (d, 2.1 Hz, 1H), 5.17 (s, 2H), 4.28 (q, 7.1 Hz, 2H), 3.90 (s, 3H), 3.87 (heptet, 6.9 Hz, 1H), 1.29 (t, 7.1 Hz, 3H), 1.28 (d, 6.8 Hz, 6H). LC-MS: 3.51 min. (m/Z=305.1, 327.0).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customPartition the residue between EtOAc and water
  3. extractionExtract the aqueous layer with EtOAc several times
  4. extractionThe combined organic extract
  5. washwas washed with water (3×) and saturated brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated
  8. customto give the crude product

出典と根拠

ORDレコード
ord-61b7c45b7a3d44cc8f95aa2962e2dba1
出典データセット
uspto-grants-2009_07
特許番号
US07563816B2

反応ノート

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