Cesium carbonate → 1-(2,2-Dimethoxyethyl)-5-iodo-1H-indazole

HRID 2387506ノート

反応式

HRID 2387506 の反応式
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14]Br.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O.CCOC(C)=O>[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][N:7]1[C:8]2[C:4](=[CH:3][C:2]([I:1])=[CH:10][CH:9]=2)[CH:5]=[N:6]1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 218947395-Iodo-1H-indazole

生成物 1

HCID 576255361-(2,2-Dimethoxyethyl)-5-iodo-1H-indazole収率 46%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

To a solution of 5-iodio-1H-indazole (8.28 g, 33.9 mmol) in DMSO (104 mL) was added 2-bromoacetaldehyde dimethyl acetal (7.9 mL, 68 mmol) and Cs2CO3 (44.1 g, 136 mmol). The reaction mixture was stirred at 40° C. for 18 h; then the reaction mixture was diluted with H2O (100 mL) and EtOAc (175 mL). The partitioned material was extracted with EtOAc (4×175 mL). The organics were washed with brine (2×100 mL), dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography (silica gel, hexanes with 0.1% Et3N/EtOAc with 0.1% Et3N, 100:0 to 90:10) gave the title compound (4.49 g, 46%) as a light orange powder. 1H NMR (500 MHz, CDCl3) δ 8.07 (d, J=1.0 Hz, 1H), 7.92 (d, J=0.5 Hz, 1H), 7.60 (dd, J=9.0, 1.5 Hz, 1H), 7.28 (d, J=9.0 Hz, 1H), 4.71 (t, J=5.5 Hz, 1H), 4.44 (d, J=5.5 Hz, 2H), 3.33 (s, 6H).

後処理

  1. extractionThe partitioned material was extracted with EtOAc (4×175 mL)
  2. washThe organics were washed with brine (2×100 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (silica gel, hexanes with 0.1% Et3N/EtOAc with 0.1% Et3N, 100:0 to 90:10)

出典と根拠

ORDレコード
ord-26f0c7ecfb054d2bb9fb10b7b3c24e90
出典データセット
uspto-grants-2012_09
特許番号
US08268868B2

反応ノート

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