Water → 2-phenyl-N-(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)acetamide

HRID 734964노트

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HRID 734964 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][C:13](=[O:21])[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:30]2[CH:31]=[C:32]([NH:36][S:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)(=[O:39])=[O:38])[CH:33]=[N:34][CH:35]=2)O1.O>C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.[Cl-].[Na+].O>[C:15]1([CH2:14][C:13]([NH:12][C:8]2[CH:7]=[N:6][C:5]3[C:10](=[CH:11][C:2]([C:30]4[CH:35]=[N:34][CH:33]=[C:32]([NH:36][S:37]([C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=5)(=[O:39])=[O:38])[CH:31]=4)=[CH:3][CH:4]=3)[N:9]=2)=[O:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 52936632N-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzenesulfonamideHCID 68509491N-(7-bromo-2-quinoxalinyl)-2-phenylacetamide

생성물 1

HCID 578433632-phenyl-N-(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)acetamide수율 33.4%

시약·촉매·용매 3

HCID 10340Sodium Carbonate용매HCID 312751,4-Dioxane용매HCID 57417360Sodium chloride; water용매

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온도
100 °C

실험 절차

A mixture of N-(7-bromo-2-quinoxalinyl)-2-phenylacetamide (0.254 mmol), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (0.508 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.007 mmol) in 2M aqueous sodium carbonate (0.5 mL) and 1,4-dioxane (2 mL) was heated at 100° C. for 5 h. The reaction mixture was cooled, poured into water (60 mL) and brine (15 mL), and extracted with ethyl acetate (50 mL). The aqueous layer was acidified with 1N aqueous HCl until the pH was approximately 6-7 and then further extracted with (3×50 mL) ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography eluting with 50-70% ethyl acetate/hexanes followed by reverse phase HPLC (30-75% acetonitrile/water with 0.1% TFA) afforded the title product as a tan solid (42 mg, 33%). MS(ES)+ m/e 496 [M+H]+.

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (50 mL)
  3. extractionfurther extracted with (3×50 mL) ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by silica gel chromatography
  8. washeluting with 50-70% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-6e6d12b4db544d718eb25537c78acfaa
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592342B2

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