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

HRID 734964ノート

反応式

HRID 734964 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 10340Sodium Carbonate溶媒HCID 312751,4-Dioxane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-6e6d12b4db544d718eb25537c78acfaa
出典データセット
uspto-grants-2009_09
特許番号
US07592342B2

反応ノート

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