Potassium Iodide → [4-(5-Ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-vinyl-naphthalen-2-yl]-acetic acid methyl ester

HRID 238645노트

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HRID 238645 반응식
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[C:14]([CH:15]=[CH2:16])=[C:13]([OH:17])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:18])[CH:11]=2)[CH:6]=1.C(S([C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH2:34][CH3:35])(=[O:33])=[O:32])=[CH:27][N:26]=1)(=O)=O)C.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O.CN(C)C=O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[C:14]([CH:15]=[CH2:16])=[C:13]([O:17][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH2:34][CH3:35])(=[O:32])=[O:33])=[CH:27][N:26]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:18])[CH:11]=2)[CH:6]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 132780152,5-Bis(ethylsulfonyl)pyridineHCID 59326580(6-Fluoro-4-hydroxy-3-vinyl-naphthalen-2-yl)-acetic acid methyl ester

생성물 1

HCID 59326526[4-(5-Ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-vinyl-naphthalen-2-yl]-acetic acid methyl ester수율 36.1%

시약·촉매·용매 2

HCID 180Acetone용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A mixture of (6-fluoro-4-hydroxy-3-vinyl-naphthalen-2-yl)-acetic acid methyl ester (22 mg, 0.084 mmol), 2,5-bis-ethanesulfonyl-pyridine (33 mg, 0.126 mmol), potassium iodide (5 mg), and cesium carbonate (68 mg, 0.21 mmol), N,N-dimethylformamide (0.5 mL) and acetone (1.5 mL) was heated at 100° C. for 30 minutes with microwave irradiation. The mixture was then concentrated in vacuo. The residue was purified by flash column (gradient elution with 0-50% ethyl acetate in petroleum ether) to afford [4-(5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-vinyl-naphthalen-2-yl]-acetic acid methyl ester (13 mg, 36.1%) as a yellow solid.

후처리

  1. concentrationThe mixture was then concentrated in vacuo
  2. customThe residue was purified by flash column (gradient elution with 0-50% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-958e24f4586e40a0986164d174043df5
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642629B2

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