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

HRID 1746224Notes

Reaction equation

HRID 1746224 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 178525892HCID 178525892, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

[(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).

Workup

  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

Sources & evidence

ORD record
ord-bd5bfa11057f4d5fa8b0f1a7d7fd623e
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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