1,2-Dimethoxyethane → HCID 86703320, compound

HRID 2410005Notes

Reaction equation

HRID 2410005 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].COCCOC.Br[C:14]1[CH:15]=[N:16][CH:17]=[N:18][CH:19]=1.[C:20]([O:24][C:25]([N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=2)[CH:29]=[C:28]1B(O)O)=[O:26])([CH3:23])([CH3:22])[CH3:21]>O.[Cl-].[Na+].O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:37][O:36][C:33]1[CH:34]=[C:35]2[C:30]([CH:29]=[C:28]([C:14]3[CH:15]=[N:16][CH:17]=[N:18][CH:19]=3)[N:27]2[C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 783445-BromopyrimidineHCID 223094576-Methoxy-1H-indole-2-boronic acid, N-BOC protected

Product 1

HCID 86703320HCID 86703320, compoundYield 54.6%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

Sodium carbonate (364 mg) was dissolved in water (3.44 mL). 1,2-Dimethoxyethane (13.7 mL), 5-bromopyrimidine (273 mg), [1-(tert-butoxycarbonyl)-6-methoxy-1H-indol-2-yl]boronic acid (500 mg) and tetrakis(triphenylphosphine)-palladium(0) (99.2 mg) were added thereto, and the mixture was stirred at 100° C. for 1 hour under microwave irradiation. The reaction mixture was left to be cooled. To the reaction mixture was added a mixed solution of water and saturated brine (each 10 mL), followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (305 mg). 1H-NMR (CDCl3) δ ppm: 1.41 (9H, s), 3.91 (3H, s), 6.60-6.64 (1H, m), 6.94 (1H, dd, J=2.3, 8.7 Hz), 7.47 (1H, d, J=8.7 Hz), 7.83 (1H, d, J=2.3 Hz), 8.78 (2H, s), 9.17 (1H, s).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-b636738fd5e9448a87ca61eabf623764
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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