Ethanol → 2-(Benzofuran-2-carbonylamino)-4-(4-methyl-3-nitro-phenyl)thiophene-3-carboxylic acid

HRID 390782노트

반응식

HRID 390782 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[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][C:35]=1[N+:43]([O-:45])=[O:44].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[CH:38]=[CH:39][C:34]([CH3:33])=[C:35]([N+:43]([O-:45])=[O:44])[CH:36]=2)[C:17]=1[C:18]([OH:20])=[O:19])=[O:11]

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27735154-Methyl-3-nitrobenzeneboronic acidHCID 59225740Tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate

생성물 1

HCID 595360142-(Benzofuran-2-carbonylamino)-4-(4-methyl-3-nitro-phenyl)thiophene-3-carboxylic acid수율 81.7%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate (82, 50 mg, 0.102 mmol), 4-methyl-3-nitrophenylboronic acid (28 mg, 0.153 mmol), Tetrakis(triphenylphosphine)palladium(0) (1.0 mg, 0.001 mmol), and sodium carbonate (42 mg, 0.407 mmol), 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, triturated in methanol, centrifuged, decanted and the resulting solid was dried under vacuum and 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 84 as a white powder (35.2 mg, 43%). 1H NMR (500 MHz, DMSO d6) δ=13.48 (br, 1 H), 12.57 (br, 1 H), 7.96 (s, 1 H), 7.86 (m, 2 H), 7.76 (d, 1 H), 7.64 (d, 1 H), 7.57 (t, 1 H), 7.49 (d, 1 H), 7.42 (t, 1 H), 2.55 (s, 3 H) ppm.

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. customtriturated in methanol
  8. customdecanted
  9. customthe resulting solid was dried under vacuum
  10. additiontreated with a 1:1 mixture of methylene chloride and trifluoroacetic acid
  11. concentrationAfter 4 hours the mixture was concentrated in vacuo
  12. customthe residue triturated in methylene chloride
  13. customdecanted
  14. customdried under high vacuum

출처 및 근거

ORD 기록
ord-6156b26d4eae44c9b33fb49456e4944e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383670B2

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