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Water → Isoquinoline, 1-benzo[b]thien-2-yl-

HRID 467384
Notes
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Reaction equation

HRID 467384 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[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.C(O)C.[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[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10340Sodium CarbonateHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 251368Isoquinoline, 1-benzo[b]thien-2-yl-Yield 79%

Reagents, catalysts & solvents 3

HCID 23938
Palladium
Catalyst
HCID 702EthanolSolvent
HCID 1140TolueneSolvent

Procedure

Benzo[b]thiophene-2-ylboronic acid (997 mg, 5.6 mmol) and 1-chloroisoquinoline (946 mg, 5.8 mmol) were dissolved in toluene (20 ml) and ethanol (10 ml), and palladium catalyst (220 mg, 0.19 mmol) and 2M sodium carbonate solution (20 ml) were added thereto, 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: 1.16 g, yield: 79%).

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: 1.16 g, yield: 79%)

Sources & evidence

ORD record
ord-7c98e88a3df4448fa6806a86354cfdb8
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08623239B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes