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Water → Methyl 2'-cyano-5-(5-methylpyridin-2-yl)-5'-(trifluoromethyl)biphenyl-3-carboxylate

HRID 2278723
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HRID 2278723 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16](B3OC(C)(C)C(C)(C)O3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:7]=1.Br[C:28]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:29]=1[C:30]#[N:31].C(=O)([O-])[O-].[Cs+].[Cs+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[C:30]([C:29]1[CH:32]=[CH:33][C:34]([C:36]([F:37])([F:38])[F:39])=[CH:35][C:28]=1[C:16]1[CH:17]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)[CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:15]=1)#[N:31]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 30158022-Bromo-4-(trifluoromethyl)benzonitrileHCID 59432564Methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

생성물 1

HCID 58449399Methyl 2'-cyano-5-(5-methylpyridin-2-yl)-5'-(trifluoromethyl)biphenyl-3-carboxylate

시약·촉매·용매 2

HCID 67553
Tetrabutylammonium Iodide
촉매
HCID 6228Dimethylformamide용매

실험 절차

Into a 5 mL microwave vial were charged methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (300 mg, 0.85 mmol), 2-bromo-4-(trifluoromethyl)benzonitrile (425 mg, 1.70 mmol), cesium carbonate (1.38 g, 4.25 mmol), tetra-n-butylammonium iodide (314 mg, 0.85 mmol), POPd (43 mg, 0.085 mmol), water (0.6 mL) and N,N-dimethylformamide (3 mL). The reaction mixture was subjected to microwave irradiation at 150° C. for 10 mins. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was washed with brine, dried, and concentrated under reduced pressure to afford the residue which was purified by silica gel column to yield the title compound.

후처리

  1. customirradiation at 150° C. for 10 mins
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with ethylacetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto afford the residue which
  8. customwas purified by silica gel column

출처 및 근거

ORD 기록
ord-088f1dc84df64f43ac47bef8e5d1a8dc
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133122B2

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