Cesium carbonate → HCID 58930518, compound

HRID 416221Notes

Reaction equation

HRID 416221 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:22]=[CH:21][C:11]([O:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.Cl.[NH2:24][CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:15]1([CH2:14][CH2:13][O:12][C:11]2[CH:21]=[CH:22][C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:24][CH2:25][C:26]4[CH:27]=[CH:28][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:34][CH:35]=4)[N:7]=3)=[CH:9][CH:10]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 58930607HCID 58930607, compound

Product 1

HCID 58930518HCID 58930518, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 19 (2.7 g, 8.4 mmol) and methyl 4-(aminomethyl)benzoate hydrochloride (2.7 g, 13.5 mmol) in dry toluene (33 mL) was added cesium carbonate (8.2 g, 25.3 mmol) followed by Pd2(dba)3 (464 mg, 0.51 mmol) and rac-BINAP (473 mg, 0.76 mmol). The solution was degassed and heated at 100° C. for 16 h. The reaction mixture was partitioned between water and EtOAc and the phases were separated. The organic layer was successively washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to form a residue which was purified by flash chromatography on silica gel (MeOH/CH2Cl2: 2/98) to afford the title compound 20 (1.9 g, 4.2 mmol, 50% yield).

Workup

  1. customThe solution was degassed
  2. customThe reaction mixture was partitioned between water and EtOAc
  3. customthe phases were separated
  4. washThe organic layer was successively washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto form a residue which
  9. customwas purified by flash chromatography on silica gel (MeOH/CH2Cl2: 2/98)

Sources & evidence

ORD record
ord-e444a8feea794920839ec9f6013ce9ad
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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