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Sodium hydride → Methyl 5-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)picolinate

HRID 632652
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HRID 632652 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[H-].[Na+].Br[C:15]1[C:19]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:18]=2[S:17](=[O:26])[C:16]=1[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1>CN(C=O)C>[CH3:25][O:24][C:22]1[CH:21]=[CH:20][C:19]2[C:15]([O:1][C:2]3[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=3)=[C:16]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[S:17](=[O:26])[C:18]=2[CH:23]=1
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5

반응물 3

HCID 24758Sodium hydrideHCID 4715126Methyl 5-hydroxypyridine-2-carboxylateHCID 159594683-Bromo-6-methoxy-2-(4-methoxyphenyl)benzothiophene 1-oxide

생성물 1

HCID 86730670Methyl 5-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)picolinate수율 52.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl 5-hydroxypyridine-2-carboxylate (0.273 g, 1.78 mmol) in DMF (6.84 mL) at room temperature was added sodium hydride (60% suspension in oil, 0.043 g, 1.78 mmol) and the resulting mixture was stirred at room temperature for 30 mins. After 30 min at room temperature 3-bromo-6-methoxy-2-(4-methoxyphenyl)benzothiophene 1-oxide (0.5 g, 1.37 mmol) was added and the reaction was heated to 80° C. for 18 h. Upon completion the reaction was cooled to room temperature, quenched with water and extracted with DCM. The organic layers were combined, passed through a phase separator and concentrated in vacuo to give the crude product, which was purified by column chromatography (SiO2, 0-75% EtOAc/heptane) to afford methyl 5-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)picolinate (314 mg, 0.72 mmol, 52% yield). 1H NMR (400 MHz, CDCl3) δ ppm=3.73 (s, 3H), 3.84 (s, 3 H), 3.90-3.92 (m, 3 H), 6.79-6.86 (m, 2 H), 6.91 (dd, J=8.59, 2.53 Hz, 1 H), 7.03 (d, J=8.59 Hz, 1 H), 7.30 (dd, J=8.59, 3.03 Hz, 1 H), 7.48 (d, J=2.53 Hz, 1 H), 7.55-7.60 (m, 2 H), 7.95 (d, J=8.59 Hz, 1 H), 8.55 (d, J=2.02 Hz, 1 H), LC/MS (m/z, MH+): 438.2.

후처리

  1. temperaturethe reaction was heated to 80° C. for 18 h
  2. temperatureUpon completion the reaction was cooled to room temperature
  3. customquenched with water
  4. extractionextracted with DCM
  5. concentrationconcentrated in vacuo
  6. customto give the crude product, which
  7. customwas purified by column chromatography (SiO2, 0-75% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-64aa5922af264b3abe9093f44ea9b21e
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321746B2

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