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Ethanol → 2-(Benzofuran-2-carbonylamino)-4-(8-methyl-5-quinolyl)thiophene-3-carboxylic acid

HRID 1013556
Notes
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Reaction equation

HRID 1013556 reaction equation
[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:35]=[CH:36][C:37](B(O)O)=[C:38]2[C:43]=1[N:42]=[CH:41][CH:40]=[CH:39]2.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:36]=[CH:35][C:34]([CH3:33])=[C:43]3[C:38]=2[CH:39]=[CH:40][CH:41]=[N:42]3)[C:17]=1[C:18]([OH:20])=[O:19])=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 4715077(8-Methylquinolin-5-yl)boronic acidHCID 59225740Tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate

Product 1

HCID 461866592-(Benzofuran-2-carbonylamino)-4-(8-methyl-5-quinolyl)thiophene-3-carboxylic acidYield 31%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate (7), (8-methyl-5-quinolyl)boronic acid (48), 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, 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 49A as a white powder (18.1 mg, 31%). 1H NMR (500 MHz, DMSO d6) δ=12.93 (br, 1 H), 12.60 (s, 1 H), 8.94 (m, 1 H), 8.01 (d, 1 H), 7.89 (s, 1 H), 7.87 (d, 1 H), 7.75 (d, 1 H), 7.66 (d, 1 H), 7.57 (t, 1 H), 7.54 (dd, 1 H), 7.44-7.41 (m, 3 H), 7.11 (s, 1 H), 2.76 (s, 3 H) ppm. ESI MS [M+H] 429.22.

Workup

  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

Sources & evidence

ORD record
ord-2bd69fef275646f7bc147cff2a47a7eb
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981925B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes