Hydrochloric Acid → HCID 89782106, compound

HRID 1056031Notes

Reaction equation

HRID 1056031 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([F:12])[CH:8]=[N:7]2.C([Sn](CCCC)(CCCC)[C:18]([O:20]CC)=[CH2:19])CCC.Cl.CCN(CC)CC>C1(C)C=CC=CC=1.C1COCC1.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.CC(C)=O>[F:12][C:9]1[CH:8]=[N:7][C:6]2[C:11]([N:10]=1)=[C:2]([C:18](=[O:20])[CH3:19])[CH:3]=[CH:4][CH:5]=2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 89782160HCID 89782160, compound

Product 1

HCID 89782106HCID 89782106, compoundYield 10,628%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 180AcetoneSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-bromo-2-fluoroquinoxaline (2.36 g, 10.39 mmol), tributyl(1-ethoxyvinyl)stannane (3.86 ml, 11.43 mmol; Aldrich), and Pd(PPh3)4 (0.360 g, 0.312 mmol) in toluene (74 ml) and THF (29 ml) was heated to reflux for 1.5 h. The reaction mixture was cooled to RT before conc. HCl (1.083 ml, 12.99 mmol) was added to convert the silyl enol ether to the methyl ketone. After stirring for 5 min, Et3N (3.62 ml, 26.0 mmol) was added to quench the HCl. The crude material was concentrated, taken up in DCM, adsorbed onto silica, and purified via automated flash chromatography (silica gel) with 100% hexanes to 60% DCM in hexanes to give 1-(3-fluoroquinoxalin-5-yl)ethanone (210 g, 87% yield) as a pale yellow solid. MS (ESI, pos. ion) m/z: 191.0 (M+1).

Workup

  1. temperatureto reflux for 1.5 h
  2. additionwas added
  3. customto quench the HCl
  4. concentrationThe crude material was concentrated
  5. custompurified

Sources & evidence

ORD record
ord-a9b61ba38dee4a548943c8ad03d0be0d
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…