Potassium Phosphate, Tribasic → Methyl [4-(3-cyclopropylpyrazin-2-yl)phenyl]acetate

HRID 474144

反応式

HRID 474144 の反応式
Cl[C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:19]1([C:2]2[C:3]([C:8]3[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=3)=[N:4][CH:5]=[CH:6][N:7]=2)[CH2:21][CH2:20]1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 59535943Methyl 2-(4-(3-chloropyrazin-2-yl)phenyl)acetate

生成物 1

HCID 59535940Methyl [4-(3-cyclopropylpyrazin-2-yl)phenyl]acetate収率 65.4%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To a solution of 0.15 g (0.57 mmol) of methyl [4-(3-chloropyrazin-2-yl)phenyl]acetate acid in 3.0 mL of toluene and 0.15 mL of water were added 63.8 mg (0.74 mmol) of cyclopropyl boronic acid, 16 mg (0.06 mmol) of tricyclohexylphosphine, 7.8 mg (0.009 mmol) of Pd2(dba)3, and 0.42 g (2.0 mmol) of potassium phosphate. The resulting suspension was degassed for 10 minutes. After 1 h in the microwave at 140° C., the reaction mixture was cooled, diluted with CH2Cl2, wash three times with water, and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-40% EtOAc in hexanes) afforded 0.10 g (65%) methyl [4-(3-cyclopropylpyrazin-2-yl)phenyl]acetate. 1H NMR (CDCl3, 400 MHz) δ 8.35 (m, 2H); 7.68 (d, J=8.06 Hz, 2H); 7.41 (d, J=8.06 Hz, 2H); 3.72 (s, 3H); 3.71 (s, 2H); 2.22 (m, 1H); 1.19 (m, 2H); 0.99 (m, 2H). ES-MS M+1=269.1.

後処理

  1. customThe resulting suspension was degassed for 10 minutes
  2. temperaturethe reaction mixture was cooled
  3. additiondiluted with CH2Cl2
  4. washwash three times with water
  5. washwashed with brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography (silica gel, linear gradient 0-40% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-6249aada39304de5ad02af7adb819570
出典データセット
uspto-grants-2014_01
特許番号
US08637513B2

関連ノート

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