Methyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate → Methyl 2'-cyano-4'-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxylate

HRID 1845305노트

반응식

HRID 1845305 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:18][C:19]1[CH:20]=[CH:21][C:22](B2OC(C)(C)C(C)(C)O2)=[C:23]([CH:26]=1)[C:24]#[N:25]>CN(C)C=O.C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:24]([C:23]1[CH:26]=[C:19]([CH3:18])[CH:20]=[CH:21][C:22]=1[C:2]1[CH:11]=[C:10]([CH:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=1)#[N:25]

참가 물질

7

반응물 2

HCID 58188392Methyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoateHCID 584073295-Methyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

생성물 1

HCID 58188274Methyl 2'-cyano-4'-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxylate

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of methyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate (300 mg, 0.96 mmol), 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (280 mg, 1.1 mmol), tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.052 mmol) in N,N-dimethylformamide (0.75 mL) and toluene (1.5 mL) under nitrogen was subjected to microwave irradiation at 110° C. for 1 h. After cooling, the mixture was diluted with water (15 mL) and extracted with EtOAc (20 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash chromatography to afford the title compound.

후처리

  1. customirradiation at 110° C. for 1 h
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc (20 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-dc6818cd730941c9b05f985ae6ff2935
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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