Dimethylformamide → Methyl 2'-cyano-5-(1,2-dihydroxyethyl)-4'-methylbiphenyl-3-carboxylate

HRID 1845310ノート

反応式

HRID 1845310 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]([OH:15])[CH2:13][OH:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:16][C:17]1[CH:18]=[CH:19][C:20](B2OC(C)(C)C(C)(C)O2)=[C:21]([CH:24]=1)[C:22]#[N:23].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>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.C1(C)C=CC=CC=1>[C:22]([C:21]1[CH:24]=[C:17]([CH3:16])[CH:18]=[CH:19][C:20]=1[C:2]1[CH:11]=[C:10]([CH:12]([OH:15])[CH2:13][OH:14])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=1)#[N:23]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 58188335Methyl 3-bromo-5-(1,2-dihydroxyethyl)benzoateHCID 584073295-Methyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

生成物 1

HCID 58187958Methyl 2'-cyano-5-(1,2-dihydroxyethyl)-4'-methylbiphenyl-3-carboxylate

試薬・触媒・溶媒 3

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

実験手順

A mixture of methyl 3-bromo-5-(1,2-dihydroxyethyl)benzoate (100 mg, 0.36 mmol), 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (130 mg, 0.54 mmol), tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.035 mmol), potassium carbonate (75 mg, 0.54 mmol), N,N-dimethylformamide (0.5 mL), and toluene (1 mL) under nitrogen was subjected to microwave irradiation at 110° C. for 1 h. After cooling, the mixture was diluted with water (5 mL) and extracted with EtOAc (15 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by flash column to afford the title compound.

後処理

  1. customirradiation at 110° C. for 1 h
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc (15 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column

出典と根拠

ORDレコード
ord-9c255834da3a4232aeb48a142ef71389
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

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