Potassium Carbonate → Quinazoline

HRID 454025ノート

反応式

HRID 454025 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8](OCC3CCN(CCS(C)(=O)=O)CC3)=[C:9](OC)[CH:10]=2)[N:5]=[CH:4][N:3]=1.OC1C=C2C(=CC=1)NC(C)=C2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[N:3][CH:4]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 833362-methyl-1H-indol-5-olHCID 220305344-Chloro-6-methoxy-7-((1-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)quinazoline

生成物 1

HCID 9210Quinazoline収率 164.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A solution of 4-chloro-6-methoxy-7-((1-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)quinazoline (115 mg, 0.28 mmol), (prepared as described for the starting material in Example 12), 5-hydroxy-2-methylindole (50 mg, 0.33 mmol) and potassium carbonate (60 mg, 0.42 mmol) in DMF (1.5 ml) was stirred at 100° C. for 2 hours. After cooling, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by chromatography eluting with ethyl acetate/methylene chloride (1/1) followed by methanol/ethyl acetate/methylene chloride (1/4/5 and 1/0/9) to give 6-methoxy-4-(2-methylindol-5-yloxy)-7-41-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)quinazoline (60 mg, 41%).

後処理

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by chromatography
  7. washeluting with ethyl acetate/methylene chloride (1/1)

出典と根拠

ORDレコード
ord-24fee55cdc414c76a709b19a952401d6
出典データセット
uspto-grants-2013_07
特許番号
US08492560B2

反応ノート

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