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 1180914ノート

反応式

HRID 1180914 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-8f977e2f8770409e9c8b1bdfe52de1db
出典データセット
uspto-grants-2007_10
特許番号
US07282588B2

反応ノート

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