Acetonitrile → HCID 90418212, 화합물

HRID 923692노트

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HRID 923692 반응식
[NH2:1][C:2]1[C:7]([F:8])=[C:6](Br)[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:3]=1[Cl:14].[S:15]1[C:19]2[CH:20]=[CH:21][C:22](B(O)O)=[CH:23][C:18]=2[N:17]=[CH:16]1.[F-].[K+].CC#N>ClCCl.CC([O-])=O.CC([O-])=O.[Pd+2].O>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:22]2[CH:21]=[CH:20][C:19]3[S:15][CH:16]=[N:17][C:18]=3[CH:23]=2)[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:3]=1[Cl:14]

참가 물질

8

반응물 4

HCID 6342AcetonitrileHCID 522689Potassium FluorideHCID 18452959HCID 18452959, 화합물HCID 71551894Methyl 4-amino-6-bromo-3-chloro-5-fluoropicolinate

생성물 1

HCID 90418212HCID 90418212, 화합물수율 51%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
150 °C

실험 절차

To a 5 mL microwave vial was added methyl 4-amino-6-bromo-3-chloro-5-fluoropicolinate (200 mg, 1.0 mmol), benzo[d]thiazol-5-ylboronic acid (237 mg, 1.35 mmol), potassium fluoride (KF; 122 mg, 2.12 mmol), TPPTS-Na (tris-(3-sulfornatophenyl)-phosphine4-hydrate sodium salt, 67 mg, 0.106 mmol) and Pd(OAc)2 (11 mg, 0.053 mmol). Subsequently, CH3CN (1.0 mL) and H2O (3.0 mL) were added, and the reaction vial was sealed and heated in a Biotage microwave at 150° C. for 5 min, with external IR-sensor temperature monitoring from the side of the vessel. The reaction mixture was cooled to room temperature and diluted with dicloromethane, and washed wth water. The organic extracts were combined, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by triturating with Et2O to yield the title compound as a brown solid (172 mg, 51%).

후처리

  1. customthe reaction
  2. customvial was sealed
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washwashed wth water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified
  9. customby triturating with Et2O

출처 및 근거

ORD 기록
ord-dafc6c759c97436dba1f3cf3e64c8984
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278985B2

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