Water → 5-(1H-pyrrolo[2,3-b]pyridin-5-yl)-pyridine-2-carboxylic acid ethylamide

HRID 217598Notes

Reaction equation

HRID 217598 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)O1.[CH2:19]([NH:21][C:22]([C:24]1[CH:29]=[CH:28][C:27](Br)=[CH:26][N:25]=1)=[O:23])[CH3:20].O>C(=O)([O-])[O-].[K+].[K+].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>[CH2:19]([NH:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([C:9]2[CH:10]=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)=[CH:26][N:25]=1)=[O:23])[CH3:20]

Participants

6

Reactant 3

HCID 962WaterHCID 228316215-Bromo-N-ethylpicolinamideHCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 595696015-(1H-pyrrolo[2,3-b]pyridin-5-yl)-pyridine-2-carboxylic acid ethylamideYield 108.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (37, 0.424 g, 1.74 mmol), 5-bromo-pyridine-2-carboxylic acid ethylamide (36, 0.159 g, 0.694 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.016 g, 0.014 mmol) were mixed in 1.00 M potassium carbonate in water (4.2 mL, 4.2 mmol). The reaction mixture was heated at 80° C. overnight. The two layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The crude material was purified by silica gel flash chromatography. The appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (38, 200 mg). MS (ESI) [M+H+]+=267.2.

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum
  7. customThe crude material was purified by silica gel flash chromatography
  8. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-701fcea0874b46bd911424fd3b0d9301
Source dataset
uspto-grants-2012_06
Patent number
US08198273B2

Reaction notes

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