3-Methoxyquinoxaline-5-carbaldehyde → HCID 67130948, compound

HRID 1916320Notes

Reaction equation

HRID 1916320 reaction equation
[C:1](O[K])(C)(C)C.[CH3:7][O:8][C:9]1[CH:10]=[N:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([CH:19]=O)[C:17]=2[N:18]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CCOCC>[CH3:7][O:8][C:9]1[CH:10]=[N:11][C:12]2[C:17](=[C:16]([CH:19]=[CH2:1])[CH:15]=[CH:14][CH:13]=2)[N:18]=1

Participants

6

Reactant 2

HCID 716074383-Methoxyquinoxaline-5-carbaldehydeHCID 178418922HCID 178418922, compound

Product 1

HCID 67130948HCID 67130948, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of methyltriphenylphosphonium bromide (22.78 g) in THF (200 mL) was treated with tBuOK (7.15 g) and further stirred at rt for 1 h. The mixture was cooled to 0° C. and treated with a solution of 3-methoxy-5-quinoxalinecarboxaldehyde (10.0 g; prepared according to WO 2006/021448) in THF (100 mL). The mixture was further stirred at rt for 3 h, diluted with ether and washed with water and an aq. sat. NH4Cl solution. The org. phase was dried over MgSO4 and concentrated under reduced pressure. The residue was crystallized from ether and the crystals were filtered off. The mother liquor was purified by CC (Hex/EA 1:1), affording a light orange solid (8.70 g; 88% yield).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe mixture was further stirred at rt for 3 h
  3. washwashed with water
  4. dry with materialphase was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from ether
  7. filtrationthe crystals were filtered off
  8. customThe mother liquor was purified by CC (Hex/EA 1:1)
  9. customaffording a light orange solid (8.70 g; 88% yield)

Sources & evidence

ORD record
ord-708bd1467b1a4922988db9072b8b9bb2
Source dataset
uspto-grants-2013_12
Patent number
US08618092B2

Reaction notes

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