Sodium Carbonate → {6-Chloro-3-methyl-4-[4-(piperidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester

HRID 1468414노트

반응식

HRID 1468414 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.B([C:48]1[CH:53]=[CH:52][C:51]([S:54]([N:57]2[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]2)(=[O:56])=[O:55])=[CH:50][CH:49]=1)(O)O.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:48]2[CH:53]=[CH:52][C:51]([S:54]([N:57]3[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62]3)(=[O:56])=[O:55])=[CH:50][CH:49]=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 44119543(4-(Piperidin-1-ylsulfonyl)phenyl)boronic acidHCID 86694933(6-Chloro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester

생성물 1

HCID 86695007{6-Chloro-3-methyl-4-[4-(piperidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester

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 (0.20 g, 0.50 mmol) in dimethoxyethane (10 mL) was purged with argon for 5 minutes at room temperature. Triphenylphosphine (0.030 g, 0.11 mmol), palladium (II) acetate (0.013 g, 0.055 mmol), 1-(4-boronophenylsulfonyl)piperidine (0.183 g, 0.68 mmol) and a 2 M aqueous solution of sodium carbonate (1.0 mL, 2.0 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 {6-chloro-3-methyl-4-[4-(piperidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (0.133 g, 58%) as a solid. MS calcd. for C25H25ClNO4S [(M−H)−] 470, obsd. 470.5.

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

출처 및 근거

ORD 기록
ord-d0811885f83d435fba2569938012bd90
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000044B2

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