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3,5-Bis-trifluoromethylphenylboronic acid → HCID 178525892, 화합물

HRID 1423950
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HRID 1423950 반응식
C([O:3][C:4](=[O:23])[CH2:5][NH:6][C:7]([C:9]1[C:10](=[O:22])[S:11][C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][C:15]([Cl:20])=[CH:14][C:13]=2Br)=[O:8])C.[F:24][C:25]([F:40])([F:39])[C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1>COCCOC.C1(P([Pd-4](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)C=CC=CC=1>[F:24][C:25]([F:39])([F:40])[C:26]1[CH:27]=[C:28]([C:13]2[CH:14]=[C:15]([Cl:20])[CH:16]=[C:17]3[C:12]=2[S:11][C:10](=[O:22])[C:9]([C:7]([NH:6][CH2:5][C:4]([OH:3])=[O:23])=[O:8])=[C:18]3[OH:19])[CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 178472764HCID 178472764, 화합물

생성물 1

HCID 178525892HCID 178525892, 화합물수율 74.5%

시약·촉매·용매 2

HCID 178420553HCID 178420553, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

[(8-Bromo-6-chloro-4-hydroxy-2-oxo-2H-thiochromene-3-carbonyl)-amino]-acetic acid ethyl ester (22(d)) (500 mg, 1.2 mmol) was dissolved in DME-aqueous sodium carbonate (2M) (7 mL: 1.5 mL). To the solution was added 3,5-bis-trifluoromethyl-phenyl boronic acid (372 mg, 1.44 mmol) and tetrakis(triphenylphosphino) palladium(0) (275 mg, 0.24 mmol). The mixture was heated to reflux for six hours, cooled and concentrated. The residue was triturated with hot methanol (20 mL) and filtered to provide the title compound (470 mg.) MS ESI(−) m/e: 524.114, 526.018 (M−1).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for six hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue was triturated with hot methanol (20 mL)
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-fea7c5ab8df0417eb467f8e2eec620af
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08927591B2

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