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

HRID 1727786

반응식

HRID 1727786 반응식
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:9](I)=[CH:10][C:3]=12.[CH:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].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>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:9]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:21]=[O:22])[CH:28]=3)=[CH:10][C:3]=12

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 27343563-Formylphenylboronic acidHCID 469079554-Bromo-2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 730140383-(4-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)benzaldehyde수율 77%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

In a sealed pressure tube was added 4-bromo-2-iodo-1-phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine (2.1 mmol; preparation disclosed in WO03/000690A1), 3-formylbenzeneboronic acid (2.1 mmol), N,N-dimethylformamide (15 mL), aqueous saturated sodium bicarbonate (5 mL) and tetrakis(triphenylphosphine)palladium(0) (0.1 mmol). The reaction was purged with nitrogen, capped and stirred at 100° C. for 16 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 flash chromatography by silica gel (0-4% ethyl acetate in methylene chloride) gave the title compound as a white solid (77%). ESMS [M+H]+: 441.2

후처리

  1. customThe reaction was purged with nitrogen
  2. customcapped
  3. temperatureAfter cooling to room temperature the reaction
  4. concentrationwas 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 flash chromatography by silica gel (0-4% ethyl acetate in methylene chloride)

출처 및 근거

ORD 기록
ord-89f6a322f61641569c0f46a7c7124029
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495102B2

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