Water → Ethyl 3-(5-(2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405147

반응식

HRID 405147 반응식
Br[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].CC1(C)C(C)(C)OB([C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=2)O1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(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]>[CH:4]([C:3]1[CH:6]=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:2]=1[C:22]1[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=1)=[O:5]

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30203732-Bromo-4-(trifluoromethyl)benzaldehydeHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate

생성물 1

HCID 86674249Ethyl 3-(5-(2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

2-bromo-4-(trifluoromethyl)benzaldehyde (1.3 g, 5.1 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate, prepared as in example 19, (2.7 g, 7.7 mmol), Pd(dppf)Cl2 (421 mg, 0.5 mmol), and K2CO3 (1.4 g, 10.3 mmol) were dissolved in 1,4-dioxane (40 mL) and water (10 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

후처리

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

출처 및 근거

ORD 기록
ord-f5cdc8a72be244d6966f94d960110110
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748624B2

연결된 노트

불러오는 중…