Dimethylformamide → 6-Bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalene-2-carboxylic acid methyl ester

HRID 238633노트

반응식

HRID 238633 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:16])[CH:11]=2)[CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].C(S([C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH2:37][CH3:38])(=[O:36])=[O:35])=[CH:30][N:29]=1)(=O)=O)C.CN(C)C=O>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH2:37][CH3:38])(=[O:35])=[O:36])=[CH:30][N:29]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:16])[CH:11]=2)[CH:6]=1)=[O:4]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 132780152,5-Bis(ethylsulfonyl)pyridineHCID 673054496-Bromo-4-hydroxy-naphthalene-2-carboxylic acid methyl ester

생성물 1

HCID 593266036-Bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalene-2-carboxylic acid methyl ester수율 41.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A mixture of 6-bromo-4-hydroxy-naphthalene-2-carboxylic acid methyl ester (423 mg, 1.5 mmol), potassium carbonate (414 mg, 3 mmol), 2,5-bis-ethanesulfonyl-pyridine (420 mg, 1.6 mmol) and N,N-dimethylformamide (4 mL) was vigorously stirred and heated at 100° C. overnight under an argon atmosphere, then cooled to room temperature, and diluted with ethyl acetate (10 mL). The resulting mixture was washed with water (10 mL×3). The combined aqueous layers were extracted with ethyl acetate (10 mL). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether) to give 6-bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalene-2-carboxylic acid methyl ester (280 mg, 41%, crude yield) as a yellow solid.

후처리

  1. temperaturecooled to room temperature
  2. washThe resulting mixture was washed with water (10 mL×3)
  3. extractionThe combined aqueous layers were extracted with ethyl acetate (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-e12345daf48a476eb9c1bdbe77e1553f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642629B2

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