Lithium Hexamethyldisilazide → 2-(Tert-butylsulfonyl)-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridin-3-amine

HRID 8819Notes

Reaction equation

HRID 8819 reaction equation
[C:1]([S:5]([CH2:8][O:9][C:10]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:15]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:14][C:11]=1[C:12]#[N:13])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>CN(C=O)C.C1COCC1>[C:1]([S:5]([C:8]1[O:9][C:10]2=[N:17][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])=[C:15]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[CH:14]=[C:11]2[C:12]=1[NH2:13])(=[O:6])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 219849482-[(Tert-butylsulfonyl)methoxy]-6-(2-chlorophenyl)-5-(4-chlorophenyl)-nicotinonitrile

Product 1

HCID 219848092-(Tert-butylsulfonyl)-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridin-3-amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.87 g (3.9 mmol) of the product of Step B in 24 mL of DMF at 0° C. was added 7.9 mL of a 1.0 M solution of lithium bis(trimethylsilyl)amide in THF. The reaction mixture was stirred an addition 5 min then it was quenched with 0.45 mL of acetic acid and then partitioned between ethyl acetate and saturated NaCl solution. The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was then purified via silica gel flash chromatography eluting with a gradient of 0 to 40% ethyl acetate/hexane to afford the title compound. HPLC/MS: 475.1 (M+1), 477.0 (M+3); Rt=3.99 min.

Workup

  1. additionan addition 5 min
  2. customit was quenched with 0.45 mL of acetic acid
  3. custompartitioned between ethyl acetate and saturated NaCl solution
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was then purified via silica gel flash chromatography
  9. washeluting with a gradient of 0 to 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-8aaed631857a4993a8ca04b643cc93d8
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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