Ethyl Acetate → HCID 66801724, compound

HRID 1843857Notes

Reaction equation

HRID 1843857 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[S:20][C:19]2[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=2[CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].C(OC(=O)C)C>C1(C)C=CC=CC=1.O.CCCCCC.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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[S:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=2)=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 569722892-Bromo-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one

Product 1

HCID 66801724HCID 66801724, compoundYield 88%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

(4-Fluoro-phenyl)-dihydroxy-borane (232 mg, 1.66 mmol) was added to a stirred suspension of 2-bromo-6,7-dihydro-5H-thieno[3,2-c]pyridin-4-one (I-14d: 300 mg, 1.38 mmol) and Na2CO3 (211.8 mg, 2.0175 mmol) in toluene (20 mL) and water (3 mL) with continuous argon purging. This was followed by the addition of Pd(PPh3)4 (159 mg, 0.138 mmol) and the resulting mixture was stirred at 100° C. overnight. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was filtered; the filtrate was washed with water, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (30% ethylacetate in hexane) afforded 300 mg of the product (88% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (30% ethylacetate in hexane)

Sources & evidence

ORD record
ord-f043798b35b241eda810b60166a43718
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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