Potassium Phosphate, Tribasic → 5-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine

HRID 1958099노트

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HRID 1958099 반응식
Br[C:2]1[CH:3]=[C:4]([NH2:14])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C(O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:3]=[C:4]([NH2:14])[CH:5]=[N:6][C:7]=2[O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:18][CH:17]=1

참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acidHCID 672810445-Bromo-6-(2,2,2-trifluoroethoxy)-pyridin-3-ylamine

생성물 1

HCID 672813155-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine수율 56%

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 702Ethanol용매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
100 °C

실험 절차

To a solution of 5-bromo-6-(2, 2, 2-trifluoro-ethoxy)-pyridin-3-ylamine (2.1 g, 7.74 mmol) in DME, ethanol, water (3:1:1) (50 ml) in a sealed tube were added 4-chlorophenylboronic acid (CAS Registry No. 1679-18-1) (1.8 g, 11.62 mmol) and potassium phosphate (4.9 g, 23.22 mmol), and then the reaction mixture was purged with nitrogen for 15 min. Then Pd(dppf)2Cl2 (651 mg, 0.93 mmol) was added to the reaction mixture and heated at 100° C. for 4 h. The reaction mixture was filtered off and the filter cake was washed with ethyl acetate (3×20 ml). The organic layer was washed with water, brine, dried over Na2SO4 and evaporated in vacuo to get the crude (1.9 g). The crude was purified by column chromatography (20-25% ethyl acetate/hexane) to get the desired product (1.3 g, 56%) as brown liquid. MS (LC/MS): 303.0 (M+H).

후처리

  1. filtrationThe reaction mixture was filtered off
  2. washthe filter cake was washed with ethyl acetate (3×20 ml)
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customto get the crude (1.9 g)
  7. customThe crude was purified by column chromatography (20-25% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-1ff005338fd544dda1e5c9c5863254f9
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410107B2

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