Sodium Carbonate → {6-Chloro-4-[4-(4-methoxy-benzylsulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester

HRID 1468421노트

반응식

HRID 1468421 반응식
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13](OS(C(F)(F)F)(=O)=O)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:24])[CH:11]=2)[CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:45][O:46][C:47]1[CH:66]=[CH:65][C:50]([CH2:51][NH:52][S:53]([C:56]2[CH:61]=[CH:60][C:59](B(O)O)=[CH:58][CH:57]=2)(=[O:55])=[O:54])=[CH:49][CH:48]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:59]2[CH:58]=[CH:57][C:56]([S:53](=[O:54])(=[O:55])[NH:52][CH2:51][C:50]3[CH:49]=[CH:48][C:47]([O:46][CH3:45])=[CH:66][CH:65]=3)=[CH:61][CH:60]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:24])[CH:11]=2)[CH:6]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 44119183(4-(N-(4-Methoxybenzyl)sulfamoyl)phenyl)boronic acidHCID 86694933(6-Chloro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester

생성물 1

HCID 86695012{6-Chloro-4-[4-(4-methoxy-benzylsulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester수율 71%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A stirred solution of (6-chloro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester (0.10 g, 0.25 mmol) in dimethoxyethane (5 mL) was purged with argon for 5 minutes at room temperature. Triphenylphosphine (0.015 g, 0.055 mmol), palladium (II) acetate (0.006 g, 0.027 mmol), 4-(N-(4-methoxybenzyl)sulfamoyl)phenylboronic acid (0.109 g, 0.33 mmol) and a 2 M aqueous solution of sodium carbonate (0.6 mL, 1.2 mmol) were added simultaneously to the reaction mixture at room temperature under argon. The reaction mixture was refluxed for 2 hours and then cooled to room temperature. Water was added and the mixture was extracted twice with ethyl acetate. The collected organic extracts were washed with water and then brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product, which was finally purified using flash chromatography (Biotage, 5-10% ethyl acetate-hexane) to afford {6-chloro-4-[4-(4-methoxy-benzylsulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (0.093 g, 70%) as a solid. MS calcd. for C28H25ClNO5S [(M−H)−] 522, obsd. 522.4.

후처리

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe collected organic extracts were washed with water
  4. dry with materialbrine, dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product, which
  7. customwas finally purified

출처 및 근거

ORD 기록
ord-9d2727afbc774b098fd2010fe761b351
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000044B2

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