7-Bromo-1-benzofuran → HCID 69021207、化合物

HRID 1865086ノート

反応式

HRID 1865086 の反応式
Br[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.[CH2:34]([O:36][C:37]([C:39]1[N:40]([CH3:62])[C:41](CC)=[C:42]([C:58]#[N:59])[C:43]=1[C:44]1[CH:49]=[CH:48][C:47](OS(C(F)(F)F)(=O)=O)=[CH:46][CH:45]=1)=[O:38])[CH3:35].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C.O>[CH2:34]([O:36][C:37]([C:39]1[N:40]([CH3:62])[CH:41]=[C:42]([C:58]#[N:59])[C:43]=1[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[C:7]1[CH:6]=[CH:5][C:4]2[C:8]=1[O:9][CH:10]=[CH:2][CH:3]=2)=[O:38])[CH3:35]

参加物

8

反応物 5

HCID 1136287-Bromo-1-benzofuranHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 2735133Sodium Carbonate MonohydrateHCID 57974728HCID 57974728、化合物

生成物 1

HCID 69021207HCID 69021207、化合物収率 49.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Add together 7-bromo-benzofuran (300 mg, 1.50 mmol), potassium acetate (431 mg, 2 Eq.), and bis(pinacolato)diboron (390 mg, 1.6 Eq.) in DMF (30 mL) and stir for 10 minutes while degassing with nitrogen. Add [11′bis(diphenylphosphino) ferrocene]dichloro-palladium(II) (30 mg) to the reaction mixture and stir at 80° C. for 2 hours under a nitrogen atmosphere. Cool mixture to room temperature and add 4-cyano-5-ethyl-1-methyl-3-(4-trifluoromethanesulfonyloxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester (prepared in example E-97a or E-97b) (1.3 g, 2 Eq.), 2.0M sodium carbonate/water (3.6 mL ), and [11′bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (30 mg) to the mixture and heat at 80° C. overnight. Cool to room temperature and pour into water and extract the desired product into ethyl acetate. Separate layers, and wash the organic layer once with water, dry over potassium carbonate, filter, and concentrate under reduced vacuum to give 1.08 g as a dark solid. Purify the material by silica gel chromatography (Chromatotron™) eluting with hexane/ethyl acetate 7:3 to provide 275 mg of the title compound as a white solid. Mass spectrum (m/e): 399.2 (M*+1).

後処理

  1. customwhile degassing with nitrogen
  2. stirringAdd [11′bis(diphenylphosphino) ferrocene]dichloro-palladium(II) (30 mg) to the reaction mixture and stir at 80° C. for 2 hours under a nitrogen atmosphere
  3. temperatureheat at 80° C. overnight
  4. temperatureCool to room temperature
  5. extractionextract the desired product into ethyl acetate
  6. washSeparate layers, and wash the organic layer once with water
  7. dry with materialdry over potassium carbonate
  8. filtrationfilter
  9. concentrationconcentrate under reduced vacuum
  10. customto give 1.08 g as a dark solid
  11. customPurify the material by silica gel chromatography (Chromatotron™)
  12. washeluting with hexane/ethyl acetate 7:3

出典と根拠

ORDレコード
ord-c47302b84f7c49a1bda8da84ee7a9248
出典データセット
uspto-grants-2009_12
特許番号
US07625932B2

反応ノート

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