Water → HCID 57598046, compound

HRID 1886820Notes

Reaction equation

HRID 1886820 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.[C:21](=[O:24])([O-])[O-].[Na+].[Na+].O.CO[CH2:30][CH2:31][O:32][CH3:33]>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>[CH3:33][O:32][C:31]1[CH:9]=[CH:10][C:2]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[N:4]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:3]=2)=[CH:3][C:30]=1[CH:21]=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 216691553-Bromo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57598046HCID 57598046, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

In a tube was placed boronate ester 35 (131 mg, 500 μmol), and 3 (175 mg, 500 μmol), with sodium carbonate (114 mg, 1.08 mmol) and tetrakis(triphenylphosphine)palladium(0) (22 mg, 19 μmol). Water (0.9 g) and Ethylene glycol dimethyl ether (2.1 g) were added and the mixture was deoxygenated. The tube was sealed and heated to 110 C overnight, with magnetic stirring. The crude product was extracted with ethyl acetate and water. The organics were washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product. The crude was purified via flash chromatography and eluted with a gradient from 1:1 ethyl acetate/hexane to 100% ethyl acetate to 4/4/1 ethyl acetate/hexane/7N ammonia in methanol to give 36 (98 mg, 48%).

Workup

  1. customIn a tube was placed
  2. customthe mixture was deoxygenated
  3. customThe tube was sealed
  4. temperatureheated to 110 C overnight, with magnetic stirring
  5. extractionThe crude product was extracted with ethyl acetate and water
  6. washThe organics were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give crude product
  11. customThe crude was purified via flash chromatography
  12. washeluted with a gradient from 1:1 ethyl acetate/hexane to 100% ethyl acetate to 4/4/1 ethyl acetate/hexane/7N ammonia in methanol

Sources & evidence

ORD record
ord-aa9d44be7afd48ac830d012ed9e3e183
Source dataset
uspto-grants-2013_08
Patent number
US08501446B2

Reaction notes

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