Ethanol → HCID 68950353, compound

HRID 2384884Notes

Reaction equation

HRID 2384884 reaction equation
Br[C:2]1[S:30][C:5]2[C:6](=[O:29])[N:7]([C:10]3[CH:15]=[CH:14][C:13]([O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])=[C:12]([O:27][CH3:28])[CH:11]=3)[CH2:8][CH2:9][C:4]=2[CH:3]=1.CCO.[Cl:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.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>[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([C:2]2[S:30][C:5]3[C:6](=[O:29])[N:7]([C:10]4[CH:15]=[CH:14][C:13]([O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])=[C:12]([O:27][CH3:28])[CH:11]=4)[CH2:8][CH2:9][C:4]=3[CH:3]=2)=[CH:37][CH:36]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 689482602-Bromo-6-(3-methoxy-4-triisopropylsilanyloxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one

Product 1

HCID 68950353HCID 68950353, compoundYield 80.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Dissolve 2-bromo-6-(3-methoxy-4-triisopropylsilanyloxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (2.87 g, 5.46 mmol) in dimethoxyethane (28 mL) followed by addition of EtOH (4 mL) and water (8 mL). Add 4-chlorophenylboronic acid (1.28 g, 8.19 mmol) followed by 2M Na2CO3 (4 mL, 8.19 mmol). Allow dry argon gas to bubble through the reaction mixture for 15-20 min. Add Pd(PPh3)4 (315 mg, 0.27 mmol) and then warm to 90° C. under an argon atmosphere. After 3 h, filter the reaction through Celite® and elute with CH2Cl2. Concentrate and purify via silica gel chromatography using a 0-25% gradient of EtOAc/hexanes to give 2.37 g (80% yield) of the desired product. MS/ES m/z (35Cl) 542.1 [M+H]−.

Workup

  1. customAllow dry argon gas to bubble through the reaction mixture for 15-20 min
  2. filtrationfilter
  3. customthe reaction through Celite®
  4. washelute with CH2Cl2
  5. concentrationConcentrate
  6. custompurify via silica gel chromatography

Sources & evidence

ORD record
ord-b44b871fe22045eba8bda4dd5ea4b17f
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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