Sodium Carbonate → HCID 178482645, compound

HRID 2114042Notes

Reaction equation

HRID 2114042 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=4)[CH:18]=[C:13]3[C:12](B3OC(C)(C)C(C)(C)O3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:38]1[N:39]=[CH:40][NH:41][CH:42]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([N:25]([CH3:26])[CH3:27])=[CH:21][CH:20]=4)[CH:18]=[C:13]3[C:12]([C:38]3[N:39]=[CH:40][NH:41][CH:42]=3)=[CH:11]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 59811950HCID 59811950, compoundHCID 178506559HCID 178506559, compound

Product 1

HCID 178482645HCID 178482645, compoundYield 84%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 16 (150 mg, 0.298 mmol), 4-iodoimidazole (86.7 mg, 0.447 mmol), dichlorobis(triphenylphosphine)palladium (II) (20.9 mg, 0.0298 mmol), LiCl (37.9 mg, 0.894 mmol), 1M aq. Na2CO3 (0.75 mL, 0.75 mmol) in toluene (1.8 mL) and EtOH (1.8 mL) was microwaved at 120° C. for 15 min. The reaction mixture was cooled, brine (3 mL) was added and the aqueous layer extracted with ethyl acetate (3×5 mL). Sorbent (HM-N, Jones Chromatography) was added, the solvent evaporated and the product purified by silicagel chromatography using MeOH:CH2Cl2 (3:97) (gradient elution) to give product 17 as a brown foam (111 mg, 84%); 1H NMR (400 MHz, CDCl3) δ 2.96 (s, 6H), 6.77 (d, J=8.8 Hz, 2H), 7.48-7.35 (m, 5H), 7.52 (t, J=7.6 Hz, 1H), 7.81 (s, 1H), 7.99 (s, 1H), 8.11 (d, J=7.5 Hz, 2H), 8.27 (d, J=2.0 Hz, 1H), 8.61 (d, J=2.1 Hz, 1H).

Workup

  1. customwas microwaved at 120° C. for 15 min
  2. temperatureThe reaction mixture was cooled
  3. extractionthe aqueous layer extracted with ethyl acetate (3×5 mL)
  4. additionSorbent (HM-N, Jones Chromatography) was added
  5. customthe solvent evaporated
  6. customthe product purified by silicagel chromatography

Sources & evidence

ORD record
ord-5440775cf7c44d0597d9cea3b5564640
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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