1,2-Dimethoxyethane → HCID 178458724, compound

HRID 1644592Notes

Reaction equation

HRID 1644592 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:19]2[NH:28][C:22]3=[N:23][CH:24]=[C:25](Br)[CH:26]=[C:21]3[N:20]=2)[CH:12]=[C:13]([O:15][CH:16]([CH3:18])[CH3:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:19]2[NH:28][C:22]3=[N:23][CH:24]=[C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:26]=[C:21]3[N:20]=2)[CH:12]=[C:13]([O:15][CH:16]([CH3:18])[CH3:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 178458723HCID 178458723, compound

Product 1

HCID 178458724HCID 178458724, compoundYield 100.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-(3-(benzyloxy)-5-isopropoxyphenyl)-6-bromo-3H-imidazo[4,5-b]pyridine (0.11 g), phenylboronic acid (0.05 g) and tetrakis(triphenylphosphine)palladium(0) (0.01 g) in a mixed solvent of dimethoxyethane (3.0 ml) and ethanol (1 ml) was 0.5M aqueous sodium carbonate solution (1 ml), and the mixture was subjected to microwave irradiation in a sealed reaction container and stirred at 150° C. for 4 min. After completion of the reaction, water (2 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml). The extract was washed successively with water and saturated brine and dried over magnesium sulfate. The solvent was concentrated under reduced pressure, and the obtained crystals were collected by filtration, washed with isopropyl ether and dried to give the title compound (0.11 g). 1H NMR (CDCl3) δ ppm 1.33 (6 H, d, J=6.03 Hz), 4.59-4.71 (1 H, m), 5.19 (2 H, s), 6.70 (1 H, t, J=1.88 Hz), 7.35-7.50 (9 H, m), 7.58 (1 H, s), 7.70 (2 H, d, J=6.97 Hz), 8.37 (1 H, d, J=1.70 Hz), 8.86 (1 H, d, J=1.70 Hz), 14.11 (1 H, s).

Workup

  1. customirradiation
  2. customin a sealed reaction container
  3. additionwas added to the reaction mixture
  4. extractionthe mixture was extracted with ethyl acetate (10 ml)
  5. washThe extract was washed successively with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe solvent was concentrated under reduced pressure
  8. filtrationthe obtained crystals were collected by filtration
  9. washwashed with isopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-6864f0df9b0948ec84337de2237bf8d9
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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