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Hydrochloric Acid → 3-(3-Methoxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-one

HRID 920928
Notes
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Reaction equation

HRID 920928 reaction equation
Br[C:2]1[C:6]2[C:7](=[O:23])[N:8]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[CH3:24][O:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].Cl>C(O)C.C1(C)C=CC=CC=1.CC(=O)OCC.C(Cl)Cl.CO>[CH3:24][O:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[C:2]1[C:6]2[C:7](=[O:23])[N:8]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 467390193-Methoxypyridine-4-boronic acidHCID 866831403-bromo-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-on

Product 1

HCID 866831393-(3-Methoxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-oneYield 29.8%

Reagents, catalysts & solvents

4
HCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
130 °C

Procedure

A reaction tube was charged with a solution of 3-bromo-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-on (100 mg, 0.260 mmol) in 1.5 mL of ethanol and 1.5 mL of toluene under argon. To this suspension, 3-methoxypyridin-4-ylboronic acid (39.7 mg, 0.260 mmol) and a 2M solution of Na2CO3 (41.3 mg, 0.389 mmol) were added. Then, tetrakis(triphenylphoshine)palladium (30.0 mg, 0.026 mmol) was added. The reaction mixture was heated in a Biotage microwave at about 130° C. for about 30 min. The reaction was monitored by TLC (DCM/methanol=9:1). After completion of the reaction, EA was added followed by the addition of 1 N HCl. The mixture was extracted twice with EtOAc. The organic layer was basified with NaHCO3 and extracted with brine. The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in isopropanol. Isopropanol containing HCl was added. The precipitate was sucked off and recrystallized from hot ethyl acetate to give a white solid (32 mg, 29.8%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted twice with EtOAc
  3. extractionextracted with brine
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe crude product was dissolved in isopropanol
  8. additionIsopropanol containing HCl
  9. additionwas added
  10. customrecrystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-ab9ad1bc43a842d1addd2c5e0d0d7d05
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09273068B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes