Sodium Carbonate → HCID 67061250, compound

HRID 901431Notes

Reaction equation

HRID 901431 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26].[C:30](=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>O.Cl[Pd-2](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.ClCCl.C(#N)C>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:2]2[CH:3]=[C:4]3[C:10]([CH2:11][C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:30]=4)=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 49830292HCID 49830292, compound

Product 1

HCID 67061250HCID 67061250, compoundYield 34%

Reagents, catalysts & solvents 4

HCID 178418903HCID 178418903, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A vial was charged with 50 mg (0.18 mmol) of 5-bromo-3-phenylpyrrolo[2,3-b]pyridine, 43 mg (0.24 mmol) of 3,4-dimethoxyphenylboronic acid and 6.5 mg (9.3 μmol, 5 mol %) of dichlorobis(triphenylphosphino)palladium(II). To this mixture was added 1 ml of acetonitrile and 1 ml of a 2 M aqueous solution of sodium carbonate. The vial was sealed and irradiated in a Personal Chemistry® microwave reactor with a temperature setting of 165° C. for 20 minutes. The resulting mixture was distributed between 75 ml of dichloromethane and 20 ml of a saturated aqueous solution of sodium bicarbonate in water. The organic phase was dried over sodium sulfate and evaporated. The residue obtained was recrystallized from a hot mixture of acetonitrile and ethanol to afford 20 mg (61 μmol, 34% yield) of 5-(3,4-dimethoxyphenyl)-3-phenylmethylpyrrolo[2,3-b]pyridine as a colorless crystalline solid. 1H-NMR (d6-DMSO) δ: 11.97 [1H] s, 8.55 [1H] d, 8.38 [1H] d, 7.90 [1H] d, 7.79 [2H] d, 7.45 [2H] t, 7.30 [1H] d, 7.26 [2H] t(m), 7.06 [1H] d, 3.87 [3H] s, 3.81 [3H] s. MS, m/z: 331 [MH+].

Workup

  1. customThe vial was sealed
  2. customirradiated in a Personal Chemistry® microwave reactor with a temperature setting of 165° C. for 20 minutes
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas recrystallized from a hot mixture of acetonitrile and ethanol

Sources & evidence

ORD record
ord-d6d8c76dfdbd47c180d1f3035cc07c02
Source dataset
uspto-grants-2008_04
Patent number
US07361763B2

Reaction notes

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