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

HRID 1845205노트

반응식

HRID 1845205 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-94754504cb064c59999fbde58b2c1f9b
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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