Tetrahydrofuran → HCID 86656446, compound

HRID 527967Notes

Reaction equation

HRID 527967 reaction equation
CC1CCCN(C)C1(C)C.[Li]CCCC.[F:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[C:22]([O:27][CH3:28])[C:21]([O:29][CH3:30])=[N:20]2.ClC1C(Cl)=NC2C(=CC=C(F)C=2)N=1.[NH4+].[Cl-].C1C[O:49][CH2:48]C1>CN(C=O)C>[F:16][C:17]1[CH:26]=[CH:25][C:24]2[N:23]=[C:22]([O:27][CH3:28])[C:21]([O:29][CH3:30])=[N:20][C:19]=2[C:18]=1[CH:48]=[O:49]

Participants

8

Reactant 6

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 4447681Quinoxaline, 2,3-dichloro-6-fluoro-HCID 12666545HCID 12666545, compoundHCID 187617721,2,2,3-TetramethylpiperidineHCID 178418339Butyllithium

Product 1

HCID 86656446HCID 86656446, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of tetramethylpiperidine (16.4 mL) in dry THF (100 mL) was cooled to −78° C. and treated dropwise with n-BuLi (2.5M in Hex; 39 mL). The solution was further stirred at −78° C. for 30 min. A solution of 6-fluoro-2,3-dimethoxy-quinoxaline (15.6 g; prepared from the commercially available 2,3-dichloro-6-fluoroquinoxaline according to Egyptian Journal of Chemistry (1980), Volume Date 1977, 20, 427-39) in dry THF (450 mL) was cooled to −78° C., treated dropwise with the first solution and further stirred at −78° C. for 30 min. The resulting reaction mixture was treated with DMF (11.56 mL) and further stirred at −78° C. for 15 min. The reaction mixture was poured onto a mixture of a sat. NH4Cl solution and ice and extracted with ether. The org. layer was washed with brine, dried over MgSO4, evaporated under reduced pressure and crystallised from Hex/EA affording a light yellow solid (12.5 g; 71% yield).

Workup

  1. temperaturewas cooled to −78° C.
  2. additiontreated dropwise with the first solution
  3. stirringfurther stirred at −78° C. for 30 min
  4. customThe resulting reaction mixture
  5. stirringfurther stirred at −78° C. for 15 min
  6. extractionextracted with ether
  7. washlayer was washed with brine
  8. dry with materialdried over MgSO4
  9. customevaporated under reduced pressure
  10. customcrystallised from Hex/EA affording a light yellow solid (12.5 g; 71% yield)

Sources & evidence

ORD record
ord-afb133ca8512465889c03faec961d0d8
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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