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Cesium carbonate → HCID 178525893, compound

HRID 1746223
Notes
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Reaction equation

HRID 1746223 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.[CH2:24]([B-](F)(F)F)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.C1(P([Pd-2](Cl)(Cl)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>[CH2:24]([C:13]1[CH:14]=[C:15]([Cl:20])[CH:16]=[C:17]2[C:12]=1[S:11][C:10](=[O:22])[C:9]([C:7]([NH:6][CH2:5][C:4]([OH:3])=[O:23])=[O:8])=[C:18]2[OH:19])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 23692459Potassium benzyltrifluoroboranuideHCID 178472764HCID 178472764, compound

Product 1

HCID 178525893HCID 178525893, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 178418903HCID 178418903, compoundCatalyst
HCID 21881883
Oxolane--water (1/1)
Solvent

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 THF-water (4:1; 20 mL total volume). To the solution was added potassium benzyltrifluoroborate (285 mg, 1.2 mmol), cesium carbonate (1.2 g, 3.6 mmol), and bis(triphenylphosphino) palladium(II) dichloride (168 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 (395 mg.) MS ESI(−) m/e: 402.355, 403.783 (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-8dec94aba32a49a5ae8ab913c8638c15
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09149476B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes