Toluene → HCID 44554078, compound

HRID 1254048Notes

Reaction equation

HRID 1254048 reaction equation
[Li+].C[Si]([N-:6][Si](C)(C)C)(C)C.[C:11]([O:16][CH3:17])(=[O:15])[CH:12]([CH3:14])[CH3:13].Br[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:26]=[C:27](C3C=CN=CC=3)[N:28]([CH3:38])[C:29]=2[S:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[CH:21][CH:20]=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[C:63]1(C)C=[CH:67][CH:66]=[CH:65][CH:64]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([S:30][C:29]2[N:28]([CH3:38])[C:27]([C:67]3[CH:66]=[CH:65][CH:64]=[CH:63][N:6]=3)=[N:26][C:25]=2[C:22]2[CH:21]=[CH:20][C:19]([C:12]([CH3:14])([CH3:13])[C:11]([O:16][CH3:17])=[O:15])=[CH:24][CH:23]=2)=[CH:32][CH:33]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 11039Methyl isobutyrateHCID 2733832Lithium HexamethyldisilazideHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 131730613HCID 131730613, compound

Product 1

HCID 44554078HCID 44554078, compound

Reagents, catalysts & solvents 1

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst

Procedure

LiHMDS (1.4 mL of 1 M solution in PhMe) was added to methyl isobutyrate(134 mg, 1.3 mmol) at 0° C. The solution was stirred for 10-15 min at it before it was transferred to a flask containing 2-{4-[(4-bromophenyl)-5-[(4-chlorophenyl)thio]-1-methyl-1H-imidazol-2-yl}pyridine (Example 15, 200 mg, 0.44 mmol), Pd(dba)2 (25 mg, 0.044 mmol), and tri-t-butylphosphonium tetrafluoroborate (13 mg, 0.044 mmol) in 1 mL of PhMe. After stirring at rt overnight, it was quenched with aqueous NH4Cl and the product was extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel column chromatography (5-15% EtOAc in hexanes) to give the title compound. 1H NMR (500 MHz, (CDCl3): 8.67 (d, 1H), 8.38 (d, 1H), 8.06 (d, 2H), 7.84 (t, 1H), 7.39 (d, 2H), 7.32 (t, 1H), 7.24 (d, 2H), 7.05 (d, 2H), 4.13 (s, 3H), 3.65 (s, 3H), 1.61 (s, 6H). LCMS: m/z 478 (M+H)+.

Workup

  1. customwas transferred to a flask
  2. stirringAfter stirring at rt overnight
  3. customit was quenched with aqueous NH4Cl
  4. extractionthe product was extracted with EtOAc
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel column chromatography (5-15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f4f9298566f040efbdfd36e9335450cc
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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