Water → 9-Benzothienylphenanthridine

HRID 467386Notes

Reaction equation

HRID 467386 reaction equation
[S:1]1[C:5](B(O)O)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.Cl[C:14]1[CH:15]=[CH:16][C:17]2[C:26]([CH:27]=1)=[C:25]1[C:20]([CH:21]=[CH:22][CH:23]=[CH:24]1)=[N:19][CH:18]=2.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCCC1.[Pd]>[S:1]1[C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[CH:4]=[C:5]1[C:14]1[CH:15]=[CH:16][C:17]2[C:26]([CH:27]=1)=[C:25]1[C:20]([CH:21]=[CH:22][CH:23]=[CH:24]1)=[N:19][CH:18]=2

Participants

7

Reactant 4

HCID 962WaterHCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10340Sodium CarbonateHCID 673172599-Chlorophenanthridine

Product 1

HCID 673173089-BenzothienylphenanthridineYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Benzo[b]thiophene-2-ylboronic acid (884 mg, 5.0 mmol) and 9-chlorophenanthridin (1.0 g, 4.8 mmol) were dissolved in tetrahydrofuran (30 ml), and palladium catalyst (160 mg, 0.14 mmol) and 2M sodium carbonate solution (20 ml) were added, followed by refluxing under a N2 atmosphere for 5 hours. The reaction solution was added to H2O and the mixture was extracted with chloroform, followed by drying with sodium sulfate. After filtration, the filtrate was evaporated to dryness under reduced pressure. The obtained solid was purified by column chromatography (eluent: chloroform) (amount: 1.15 g, yield: 78%).

Workup

  1. temperatureby refluxing under a N2 atmosphere for 5 hours
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialby drying with sodium sulfate
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated to dryness under reduced pressure
  6. customThe obtained solid was purified by column chromatography (eluent: chloroform) (amount: 1.15 g, yield: 78%)

Sources & evidence

ORD record
ord-48bd6ccb37be4985b64204451b59cf70
Source dataset
uspto-grants-2014_01
Patent number
US08623239B2

Reaction notes

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