2-Methyl-2-butene → 4-Amino-3-chloro-6-propyl-5-fluoropicolinic acid

HRID 508561

반응식

HRID 508561 반응식
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([CH:12]=[O:13])[C:3]=1[Cl:14].CC(=CC)C.P([O-])([O-])(O)=[O:21].[Na+].[Na+].Cl([O-])=O.[Na+]>O.C(O)(C)(C)C>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([C:12]([OH:21])=[O:13])[C:3]=1[Cl:14]

참가 물질

7

반응물 4

HCID 105532-Methyl-2-buteneHCID 24203Sodium Phosphate, DibasicHCID 23668197Sodium ChloriteHCID 867234004-Amino-3-chloro-5-fluoro-6-propylpicolinaldehyde

생성물 1

HCID 867234094-Amino-3-chloro-6-propyl-5-fluoropicolinic acid

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

반응 조건

온도
85 °C

실험 절차

A microwave vial equipped with a magnetic stir bar was charged with 4-amino-3-chloro-6-propyl-5-fluoropicolinaldehyde (15.9 mg, 0.072 mmol) and t-butanol (1.0 mL). The mixture was treated with H2O (0.40 mL), 2-methylbut-2-ene (100 μL, 0.10 mmol), sodium hydrogenphosphate (21.6 mg, 0.100 mmol), and finally sodium chlorite (19.28 mg, 0.206 mmol) was added in one portion. The mixture was heated to 85° C. for 16 h. An aliquot of the reaction mixture was analyzed by LC-MS. LC-MS analysis showed one major product with the correct mass for the desired product. The reaction mixture was evaporated to dryness under N2. Purification via reverse phase chromatography yielded 4-amino-3-chloro-6-propyl-5-fluoropicolinic acid (4.7 mg, 27.9%): 1H NMR (400 MHz, CDCl3) δ 11.60 (s, 1H), 4.98 (m, 2H), 2.76 (m, 2H), 1.75 (m, 2H), 0.99 (m, 3H); 19F NMR (376 MHz, CDCl3) δ−139.98; ESIMS m/z 231.2 ([M−H]−).

후처리

  1. customA microwave vial equipped with a magnetic stir bar
  2. additionwas added in one portion

출처 및 근거

ORD 기록
ord-f9257669cadb40fd971834e6b1dc1621
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096526B2

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