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Ethanol → 2-(Benzofuran-2-carbonylamino)-4-(4-methyl-1-naphthyl)thiophene-3-carboxylic acid

HRID 387500
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HRID 387500 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16](OS(C(F)(F)F)(=O)=O)[C:17]=1[C:18]([O:20]C(C)(C)C)=[O:19])=[O:11].[CH3:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37](B(O)O)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:37]2[C:38]3[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:34]([CH3:33])=[CH:35][CH:36]=2)[C:17]=1[C:18]([OH:20])=[O:19])=[O:11]
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참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27735114-Methyl-1-naphthaleneboronic acidHCID 59225740Tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate

생성물 1

HCID 461829372-(Benzofuran-2-carbonylamino)-4-(4-methyl-1-naphthyl)thiophene-3-carboxylic acid수율 26%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

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온도
70 °C

실험 절차

Tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate (7), (4-methyl-1-naphthyl)boronic acid (46), tetrakis(triphenylphosphine)palladium(0), and sodium carbonate were combined in 2:1:1 ethanol, toluene and water the biphasic mixture was stirred vigorously in sealed vial at 70° C. After 2 hours, the mixture was filtered through Celite and the Celite rinsed with methylene chloride. The organic fraction of the filtrate was washed with water, dried with sodium sulfate, filtered, concentrated, purified by preparative layer chromatography (10% ethyl acetate/Hexane) then treated with a 1:1 mixture of methylene chloride and trifluoroacetic acid. After 4 hours the mixture was concentrated in vacuo, and the residue triturated in methylene chloride, centrifuged, decanted and dried under high vacuum to give 47A as a white powder (12.0 mg, 26%). 1H NMR (500 MHz, DMSO d6) δ=12.80 (br, 1H), 12.60 (s, 1H), 8.04 (d, 1H), 7.88 (s, 1H), 7.87 (d, 1H), 7.74 (d, 1H), 7.57-7.52 (m, 3H), 7.46-740 (m, 2H), 7.37 (d 1H), 7.28 (d, 1H), 7.04 (s, 1H), 2.68 (s, 3H) ppm. ESI MS [M+H] 428.21.

후처리

  1. filtrationthe mixture was filtered through Celite
  2. washthe Celite rinsed with methylene chloride
  3. washThe organic fraction of the filtrate was washed with water
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by preparative layer chromatography (10% ethyl acetate/Hexane)
  8. additionthen treated with a 1:1 mixture of methylene chloride and trifluoroacetic acid
  9. concentrationAfter 4 hours the mixture was concentrated in vacuo
  10. customthe residue triturated in methylene chloride
  11. customdecanted
  12. customdried under high vacuum

출처 및 근거

ORD 기록
ord-76096a0e1ef549248530a65ff840eb4d
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08372991B2

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