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 1727787노트

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HRID 1727787 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-8a5358dfe2c54b63b0eb3f4196b936c3
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495102B2

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