Sodium Carbonate → tert-butyl N-[4-[3-(2-ethenylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 723062

반응식

HRID 723062 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O)=[CH2:2].[C:12]([O:16][C:17](=[O:38])[NH:18][C:19]([C:21]1[S:22][C:23]([S:36][CH3:37])=[C:24]([S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31](Br)[CH:30]=2)(=[O:28])=[O:27])[CH:25]=1)=[NH:20])([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[Na+].[Na+]>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.C1(C)C=CC=CC=1.CCO>[C:12]([O:16][C:17](=[O:38])[NH:18][C:19](=[NH:20])[C:21]1[S:22][C:23]([S:36][CH3:37])=[C:24]([S:26]([C:29]2[CH:30]=[C:31]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[CH:1]=[CH2:2])[CH:32]=[CH:33][CH:34]=2)(=[O:28])=[O:27])[CH:25]=1)([CH3:15])([CH3:14])[CH3:13]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27735872-Vinylbenzeneboronic acidHCID 145857672tert-butyl N-[4-(3-bromophenyl)sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

생성물 1

HCID 145857708tert-butyl N-[4-[3-(2-ethenylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 21863594Toluene ethanol용매

실험 절차

Following the procedure outlined for Examples 41–107, reaction of 2-vinyl-phenylboronic acid (30 mg, 0.20 mmol, Aldrich Chemical Company), {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (50 mg, 0.1 mmol, as prepared in Example 27, step c), tetrakis(triphenylphosphine)palladium(0) (29 mg, 0.025 mmol, Strem Chemicals, Inc., Newburyport, Mass.), Na2CO3 (400 μL, 2M aqueous), and toluene/EtOH mixture (2:1, 1.2 mL) afforded 25 mg (50%) after purification (1:3 EtOAc/hexanes, 2000μ SiO2 plate) of the title compound as a white foam.

후처리

  1. customafforded 25 mg (50%)
  2. customafter purification (1:3 EtOAc/hexanes, 2000μ SiO2 plate) of the title compound as a white foam

출처 및 근거

ORD 기록
ord-eff7796a3486439fad18f354618dcdb4
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138530B2

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