Sodium Carbonate → HCID 59699878, compound

HRID 901559Notes

Reaction equation

HRID 901559 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C([N:26]1[CH:30]=[CH:29][CH:28]=[C:27]1B(O)O)(OC(C)(C)C)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].C(#N)C>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:27]3[NH:26][CH:30]=[CH:29][CH:28]=3)[CH:3]=2)[NH:8][CH:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 596997875-Bromo-3-(2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59699878HCID 59699878, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 6342AcetonitrileSolvent

Procedure

To a Personal Chemistry® microwave vial (2-5 ml size) were added 5-bromo-3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine (96 mg, 0.32 mmol), 1-N-(BOC)pyrrole-2-boronic acid (103 mg, 0.487 mmol) and 12 mg (5 mol %) of dichloro[1,1′-bis(diphenylphoshino)ferrocene]palladium(II) dichloromethane adduct, 1 ml of acetonitrile and 1 ml of a 2 M aqueous solution of sodium carbonate. The vial was sealed, evacuated and purged three times with nitrogen, then irradiated in a Personal Chemistry® microwave reactor with a temperature setting of 150° C. for 15 minutes. Ethyl acetate (50 ml) was added, and the layers were separated. The aqueous fraction was extracted three times with ethyl acetate, and the combined organic fractions were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes gave 28.1 mg (30%) of 3-(2-methoxy-phenyl)-5-(1H-pyrrol-2-yl)-1H-pyrrolo[2,3-b]pyridine as a tan solid. 1H-NMR (d6-DMSO) δ=11.78 (br.s, 1H), 11.32 (br. s, 1H), 8.56 (d, 1H), 8.20 (d, 1H), 7.66 (d, 1H), 7.59 (dd, 1H), 7.29 (dd, 1H), 7.12 (d, 1H), 7.07 (t, 1H), 6.83 (m, 1H), 6.49 (m, 1H), 6.10 (m, 1H), 3.82 (s, 3H); MS m/z: 290 [MH]+.

Workup

  1. customThe vial was sealed
  2. customevacuated
  3. custompurged three times with nitrogen
  4. customirradiated in a Personal Chemistry® microwave reactor with a temperature setting of 150° C. for 15 minutes
  5. additionEthyl acetate (50 ml) was added
  6. customthe layers were separated
  7. extractionThe aqueous fraction was extracted three times with ethyl acetate
  8. washthe combined organic fractions were washed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-cb9d3f079e8b40c0bdbe3e4352edb658
Source dataset
uspto-grants-2008_04
Patent number
US07361764B2

Reaction notes

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