Cesium carbonate → HCID 178525893, compound

HRID 1423949Notes

Reaction equation

HRID 1423949 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

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, compoundCatalystHCID 21881883Oxolane--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-cf5062aa835445c1a0f95d80f0946e00
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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