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

HRID 1468421ノート

反応式

HRID 1468421 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9d2727afbc774b098fd2010fe761b351
出典データセット
uspto-grants-2015_04
特許番号
US09000044B2

反応ノート

読み込み中…