1,2-Dimethoxyethane → 2-(4-Methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one

HRID 423387Notes

Reaction equation

HRID 423387 reaction equation
Br[C:2]1[S:11][C:5]2[C:6](=[O:10])[NH:7][CH2:8][CH2:9][C:4]=2[CH:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+].C(COC)OC>O.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.CO>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[S:11][C:5]3[C:6](=[O:10])[NH:7][CH2:8][CH2:9][C:4]=3[CH:3]=2)=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 513419322-Bromo-5,6-dihydrothieno(2,3-c)pyridin-7(4H)-one

Product 1

HCID 576495112-(4-Methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-oneYield 82.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Combine 2-bromo-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (1.024 g, 4.42 mmol), 4-methoxyphenyl boronic acid (0.671 g, 4.42 mmol), Na2CO3 (0.94 g, 8.83 mmol), in water (10 mL), dimethoxyethane (75 mL) and CH3OH (50 mL). Purge with nitrogen for 5 min. Add Pd(PPh3)4 (0.153 g, 0.1325 mmol) and reflux the resulting mixture overnight. Cool the reaction to RT and dilute with water (100 mL). Extract with EtOAc (3×100 L), and concentrate. Treat the residue with EtOAc (40 mL), collect the solid and wash with EtOAc (20 mL) and Et2O (2×20 mL) to give the title compound (0.950 g). Concentrate the filtrate and purify the resulting residue by chromatography to give additional product (0.140 g). The overall yield is 1.090 g (95%). MS/ES m/z 260.0 [M+H]+.

Workup

  1. customPurge with nitrogen for 5 min
  2. temperatureCool
  3. customthe reaction to RT
  4. extractionExtract with EtOAc (3×100 L)
  5. concentrationconcentrate
  6. additionTreat the residue with EtOAc (40 mL)
  7. customcollect the solid
  8. washwash with EtOAc (20 mL) and Et2O (2×20 mL)

Sources & evidence

ORD record
ord-452162e5f08e492fba1673143c7f2e00
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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