Potassium Phosphate, Tribasic → HCID 57611901, compound

HRID 1919877Notes

Reaction equation

HRID 1919877 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.[C:15]1([C:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:15]1([C:21](=[N:22][CH:23]([C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=2)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 11334366Tert-butyl 4-bromobenzoate

Product 1

HCID 57611901HCID 57611901, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 1140TolueneSolvent

Procedure

Tert-butyl 4-bromobenzoate (10.3 g, 40.1 mmol), ethyl N-(diphenylmethylene)glycinate (14.99 g, 56.1 mmol), potassium phosphate (25.5 g, 120 mmol) and bis(tri-t-butylphosphine)palladium(0) (0.409 g, 0.801 mmol) were stirred in toluene (120 mL) at 100° C. under nitrogen for 3 days. Room temperature was attained and the mixture filtered through Celite and concentrated in vacuo. The residue was purified by MPLC to give the desired product as a yellow oil. 1H NMR (DMSO-d6, 600 MHz) δ 7.86 (d, J=7.8 Hz, 2H), 7.58 (m, 2H), 7.51 (m, 3H), 7.48 (d, J=7.8 Hz, 2H), 7.45 (m, 1H), 7.41 (t, J=7.5 Hz, 2H), 7.08 (m, 1H), 5.08 (s, 1H), 4.00 (m, 2H), 1.51 (s, 9H), 1.05 (t, J=6.9 Hz, 3H).

Workup

  1. customRoom temperature
  2. filtrationthe mixture filtered through Celite
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by MPLC

Sources & evidence

ORD record
ord-1aab132e021a4a6ead5396c1f6fcc46b
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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