Potassium Carbonate → Quinazoline

HRID 454025노트

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HRID 454025 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 9210Quinazoline수율 164.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-24fee55cdc414c76a709b19a952401d6
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492560B2

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