Dimethylformamide → 5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-(4-formyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

HRID 1891151노트

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HRID 1891151 반응식
[CH2:1]([NH:3][C:4]([C:6]1[C:10](I)=[C:9]([C:12]2[CH:17]=[C:16]([Cl:18])[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:14][C:13]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:8][N:7]=1)=[O:5])[CH3:2].[C:35]([O-:38])(O)=O.[Na+].CN(C=O)C>CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([NH:3][C:4]([C:6]1[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:35]=[O:38])=[CH:14][CH:13]=2)=[C:9]([C:12]2[CH:17]=[C:16]([Cl:18])[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:14][C:13]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:8][N:7]=1)=[O:5])[CH3:2]

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 592647675-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-iodo-isoxazole-3-carboxylic acid ethylamide

생성물 1

HCID 247741115-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-(4-formyl-phenyl)-isoxazole-3-carboxylic acid ethylamide수율 163.6%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-iodo-isoxazole-3-carboxylic acid ethylamide (prepared as for Example 31) (2 g, 3.4 mmol), 4-formylboronic acid (0.612 g, 4.08 mmol), NaHCO3 (10.2 ml, 1M aq. solution, 10.2 mmol), PdCl2(PPh3)2 (119 mg, 0.17 mmol) and DMF (50 ml) were combined. The mixture was then degassed by bubbling N2 through it for 5 minutes before being heated at 80° C. for 1 hour. The mixture was then evaporated in vacuo and partitioned between EtOAc (3×50 ml) and water (50 ml). The combined, dried (Na2SO4) organics were evaporated in vacuo to give a crude oil. This was dissolved in EtOAc and passed through a plug of SiO2, washing through with EtOAc. The filtrate was evaporated in vacuo and the resulting oil triturated with Et2O to afford 5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-(4-formyl-phenyl)-isoxazole-3-carboxylic acid ethylamide (1.577 g, 82%) as a pale coloured solid, LC/MS: RT=2.908 min. 567.3 (MH+).

후처리

  1. customThe mixture was then degassed
  2. customby bubbling N2 through it for 5 minutes
  3. customThe mixture was then evaporated in vacuo
  4. custompartitioned between EtOAc (3×50 ml) and water (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customorganics were evaporated in vacuo
  7. customto give a crude oil
  8. washwashing through with EtOAc
  9. customThe filtrate was evaporated in vacuo
  10. customthe resulting oil triturated with Et2O

출처 및 근거

ORD 기록
ord-be7f344f14d84e59819868267f40371e
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507480B2

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