Toluene → 2,4'-Dimethyl-5-(pyrrolidin-1-ylsulfonyl)biphenyl-3-carboxylic acid

HRID 1845205ノート

反応式

HRID 1845205 の反応式
I[C:2]1[C:3]([CH3:19])=[C:4]([CH:8]=[C:9]([S:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].B(O)(O)[C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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.O.C(O)C>[CH3:19][C:3]1[C:4]([C:5]([OH:7])=[O:6])=[CH:8][C:9]([S:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:10][C:2]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 581883403-Iodo-2-methyl-5-(pyrrolidin-1-ylsulfonyl)benzoic acid

生成物 1

HCID 581880832,4'-Dimethyl-5-(pyrrolidin-1-ylsulfonyl)biphenyl-3-carboxylic acid

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a mixture of 3-iodo-2-methyl-5-(pyrrolidin-1-ylsulfonyl)benzoic acid (1.00 g, 2.53 mmol), p-tolylboronic acid (0.378 g, 2.78 mmol), toluene (10 mL), ethanol (3 mL), cesium carbonate (0.907 g, 2.78 mmol), and water (1 mL) under argon was added tetrakis(triphenylphosphine)palladium(0) (146 mg, 0.126 mmol). The mixture was heated to reflux for 6 h, and then cooled to room temperature and filtered through Celite. The filtrate was concentrated and the residue was purified by silica gel column (0-50% EtOAc/hexane) to yield a yellow solid.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 h
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column (0-50% EtOAc/hexane)
  6. customto yield a yellow solid

出典と根拠

ORDレコード
ord-94754504cb064c59999fbde58b2c1f9b
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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