Hydrochloric Acid → 5-Chloro-4-(3-chlorophenyl)-pyridine-2-carboxylic acid

HRID 1480037

反応式

HRID 1480037 の反応式
[Cl:1][C:2]1[C:3](I)=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[C:3]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:12])[CH:18]=2)=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 855920915-Chloro-4-iodo-2-pyridinecarboxylic acid

生成物 1

HCID 902037665-Chloro-4-(3-chlorophenyl)-pyridine-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a solution of 5-chloro-4-iodo-pyridine-2-carboxylic acid (CAN 120643-06-3, 500 mg, 1.76 mmol) in toluene (10 mL) was added with stirring the [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium DCM complex (144 mg, 0.176 mmol), B-(3-chlorophenyl)-boronic acid (552 mg, 3.53 mmol) and sodium carbonate (467 mg, 4.41 mmol) in water (3 mL). The resulting mixture was stirred at 80° C. for 23 h, cooled, poured onto ice/water, acidified with hydrochloric acid (15 mL, 1 N) and partitioned between water and ethyl acetate. The organic portion was washed with brine, combined, dried over Na2SO4, filtered and concentrated. The crude product precipitated as brown solid from the concentrated solution and was used without further purification in the next step. MS (ESI, m/z): 268.1 (M).

後処理

  1. temperaturecooled
  2. additionpoured onto ice/water
  3. custompartitioned between water and ethyl acetate
  4. washThe organic portion was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product precipitated as brown solid from the concentrated solution
  9. customwas used without further purification in the next step

出典と根拠

ORDレコード
ord-2d70d6f69d29454781b85846bff6c1c6
出典データセット
uspto-grants-2016_08
特許番号
US09409866B2

関連ノート

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