Sodium Bicarbonate → 3-(4-(1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)benzaldehyde

HRID 1727787Notes

Reaction equation

HRID 1727787 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[CH:12]=3)=[CH:10][C:3]=12.[N+:28]([C:31]1[CH:36]=[CH:35][C:34]([C:37]2[C:41](B3OC(C)(C)C(C)(C)O3)=[CH:40][N:39]([CH2:51][CH3:52])[N:38]=2)=[CH:33][CH:32]=1)([O-:30])=[O:29].C(=O)(O)[O-].[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.CN(C)C=O>[N+:28]([C:31]1[CH:32]=[CH:33][C:34]([C:37]2[C:41]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[N:8]([S:19]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)(=[O:21])=[O:20])[C:9]([C:11]5[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[CH:12]=5)=[CH:10][C:3]=34)=[CH:40][N:39]([CH2:51][CH3:52])[N:38]=2)=[CH:35][CH:36]=1)([O-:30])=[O:29]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 689953481-ethyl-3-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 730140383-(4-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)benzaldehyde

Product 1

HCID 716509203-(4-(1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)benzaldehydeYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a sealed pressure tube was added 4-bromo-2-(3-formylphenyl)-1-phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine (1.6 mmol), 3-(4-nitrophenyl)-1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.7 mmol), N,N-dimethylformamide (15 mL), aqueous saturated sodium bicarbonate (4 mL) and tetrakis(triphenylphosphine)palladium(0) (0.09 mmol). The reaction was purged with nitrogen, capped, and stirred at 100° C. for 8 h. After cooling to room temperature, the reaction was concentrated under vacuum, taken up in ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered, and evaporated to dryness under vacuum. Purification by silica gel flash chromatography (5-10% ethyl acetate/methylene chloride) gave the title compound as a yellow solid (81%). ESMS [M+H]+: 578.3

Workup

  1. customThe reaction was purged with nitrogen
  2. customcapped
  3. temperatureAfter cooling to room temperature
  4. concentrationthe reaction was concentrated under vacuum
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness under vacuum
  9. customPurification by silica gel flash chromatography (5-10% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-8a5358dfe2c54b63b0eb3f4196b936c3
Source dataset
uspto-grants-2009_02
Patent number
US07495102B2

Reaction notes

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