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Toluene → 4-(5-Tert-butoxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester

HRID 723041
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HRID 723041 반응식
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][O:11][C:12]([C:14]1[S:15][C:16]([S:34][CH3:35])=[C:17]([S:19]([C:22]2[CH:27]=[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:25]=[C:24](Br)[CH:23]=2)(=[O:21])=[O:20])[CH:18]=1)=[O:13].[C:36]([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>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.CCOC(C)=O.C(O)C>[CH2:10]([O:11][C:12]([C:14]1[S:15][C:16]([S:34][CH3:35])=[C:17]([S:19]([C:22]2[CH:23]=[C:24]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:25]=[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:27]=2)(=[O:21])=[O:20])[CH:18]=1)=[O:13])[CH3:36]
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 210571734-(3-Bromo-5-tert-butoxy-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 695864274-(5-Tert-butoxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester수율 65.9%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

The procedure used in Example 1: step d was followed using benzeneboronic acid (42 mg, 0.35 mmol), 4-(3-bromo-5-tert-butoxy-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester ((Example 12: step c) (83 mg, 0.17 mmol)), Na2CO3 (2M, 1.4 mL, 2.8 mmol), Pd(PPh3)4 (48 mg, 0.04 mmol), toluene (5.6 mL), and ethanol (2.8 mL). Analogous aqueous workup and SiO2 flash chromatography (20% EtOAc in hexanes) yielded the title compound (55 mg, 65%). 1H-NMR (CDCl3): δ 8.03 (s, 1H), 7.91 (t, 1H, J=1.6 Hz), 7.63 (t, 1H, J=2.0 Hz), 7.57 (m, 2H), 7.47 (m, 2H), 7.41 (m, 2H), 4.33 (q, 2H, J=7.2 Hz), 2.60 (s, 3H), 1.42 (s, 9H), 1.36 (t, 3H, J=7.2 Hz).

출처 및 근거

ORD 기록
ord-b4343ef4b9f2416cb7c9af41026a5576
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07138530B2

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