Cesium carbonate → HCID 68313015, compound

HRID 1472918Notes

Reaction equation

HRID 1472918 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][NH:9][C@H:10]([CH:13]([CH3:15])[CH3:14])[CH2:11][OH:12])[C:5]([F:16])=[CH:4][CH:3]=1.[F:17][C:18]1[C:23]([F:24])=[C:22]([F:25])[CH:21]=[CH:20][C:19]=1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[Ca+2].[Ca+2].[Ca+2]>C(O)C.[Pd]>[F:16][C:5]1[C:6]([CH2:8][NH:9][C@H:10]([CH:13]([CH3:15])[CH3:14])[CH2:11][OH:12])=[N:7][C:2]([C:21]2[CH:20]=[CH:19][C:18]([F:17])=[C:23]([F:24])[C:22]=2[F:25])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 24456Tricalcium PhosphateHCID 27832802,3,4-Trifluorobenzeneboronic acidHCID 86671310HCID 86671310, compound

Product 1

HCID 68313015HCID 68313015, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A 4 mL vial was charged with SiliaCat DPP-Pd (0.1 equivalent., 26 mg, purchased from Silicycle). Solutions of Example 73A (20 mg, 0.07 mmol) in ethanol (1.0 mL) and 2,3,4-trifluorophenylboronic acid (14 mg, 0.08 mmol) in ethanol (0.3 mL) were added followed by 1 M aqueous Cs2CO3 (0.21 mL). The mixture was heated (Synthos 3000 Anton Paar microwave reaction system) for 30 minutes at 120° C., then filtered and concentrated. The residue was purified by reverse phase HPLC to provide the title compound. MS (ESI+) m/z 343 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-979ade129cc5423f9789d19a01c6b07f
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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