Acrylamide → ethyl 6-[(1E)-3-amino-3-oxoprop-1-enyl]-8-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854993노트

반응식

HRID 854993 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[O:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])(=O)C.[Na+].[C:49]([NH2:53])(=[O:52])[CH:50]=[CH2:51]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OC(=O)C)C.CN(C)C=O>[NH2:53][C:49](=[O:52])/[CH:50]=[CH:51]/[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[O:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2

참가 물질

8

반응물 4

HCID 6579AcrylamideHCID 80271Tri-o-tolylphosphineHCID 517045Sodium AcetateHCID 58935022ethyl 6-bromo-8-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

생성물 1

HCID 69518484ethyl 6-[(1E)-3-amino-3-oxoprop-1-enyl]-8-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate수율 61.2%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

To the mixture of 0.4 g (1.0 mmol) of ethyl 6-Bromo-8-Chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate, 45 mg (0.2 mmol) of palladium acetate, 122 mg (0.4 mmol) of tri-o-tolylphosphine, 451 mg (5.5 mmol) of sodium acetate under nitrogen atmosphere was added 6 mL of anhydrous dimethylformamide, followed by addition of 107 mg (1.5 mmol) of acrylamide. The resulting mixture was shaken at 110° C. for 85 hrs. LC-MS indicated that the reaction was done. To the reaction was added 50 mL of ethylacetate. The resulting organic solution was washed with brine and dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was purified by reverse phase chromatography to afford 0.23 g off-white solid, which was carried on to the next step.

후처리

  1. washThe resulting organic solution was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter removing the volatiles
  4. customthe residue was purified by reverse phase chromatography

출처 및 근거

ORD 기록
ord-46a50d37db154b7c8bae8a65605c666f
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259266B2

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