HCID 21943325, compound → HCID 21943316, compound

HRID 2216531Notes

Reaction equation

HRID 2216531 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:17](Br)=[C:18]([Br:20])[N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)[CH:17]=[C:18]([Br:20])[N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21943325HCID 21943325, compoundHCID 178418339Butyllithium

Product 1

HCID 21943316HCID 21943316, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 12.3 (1 g, 2.04 mmol) in THF (11 ml) at −78° C. was added 1.6 M BuLi in hexanes (1.59 ml, 2.55 mmol). The mixture was stirred at −78° C. for 0.5 h, quenched with H2O, warmed to rt, and partitioned between EtOAc and H2O. The organic phase was washed with brine, dried (Na2SO4), concentrated, and the crude product purified by SiO2 chromatography (stepwise gradient: 10 to 15 to 25% EtOAc/hexanes) to afford 723 mg (86%) of 12.4. MS (ESI) 411.3 (MH+).

Workup

  1. customquenched with H2O
  2. temperaturewarmed to rt
  3. custompartitioned between EtOAc and H2O
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customthe crude product purified by SiO2 chromatography (stepwise gradient

Sources & evidence

ORD record
ord-963740012a6846afb27453cca8984ca9
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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