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 1845305ノート

反応式

HRID 1845305 の反応式
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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dc6818cd730941c9b05f985ae6ff2935
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

読み込み中…