Sodium Carbonate → HCID 22339466, compound

HRID 1006205Notes

Reaction equation

HRID 1006205 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N:13]2[C:18](=[O:19])[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:16](=[O:28])[CH:15]=[N:14]2)=[CH:8][C:7]=1[CH3:29].[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:34][O:33][C:32]1[C:2]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:3][C:4]([O:5][C:6]2[C:11]([CH3:12])=[CH:10][C:9]([N:13]3[C:18](=[O:19])[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:16](=[O:28])[CH:15]=[N:14]3)=[CH:8][C:7]=2[CH3:29])=[CH:30][CH:31]=1

Participants

8

Reactant 3

HCID 10340Sodium Carbonate2×HCID 66827Phenylboronic Acid2×HCID 22339429HCID 22339429, compound

Product 1

HCID 22339466HCID 22339466, compoundYield 83.8%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[4-(3-bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-4-(2-trimethylsilanyl-ethoxymethyl)-2H-[1,2,4]triazine-3,5-dione (36 mg) of EXAMPLE 6 in degassed DMF (1.1 ml) were added sequentially tetrakis(triphenylphosphine)-palladium(0) (7.5 mg), phenylboronic acid (24 mg) and 2M aqueous sodium carbonate (0.13 ml). The resulting mixture was heated at 80° C. under nitrogen for 45 h, then additional portions of tetrakis(triphenylphosphine)palladium(0) (7.5 mg), phenylboronic acid (24 mg) and 2M aqueous sodium carbonate (0.13 ml) were added followed by further heating for 18 h. The reaction was diluted with water (4 ml) and extracted with ethyl acetate, then chloroform. The organic layers were washed with brine, dried and concentrated to afford the crude product (43 mg). Purification using silica gel chromatography gave the title compound (30 mg). MS Calc. 546:; Found 545 (M−1).

Workup

  1. temperatureby further heating for 18 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto afford the crude product (43 mg)
  7. customPurification

Sources & evidence

ORD record
ord-34bcf14b73a643cba125cb8c2a1e5f97
Source dataset
uspto-grants-2004_09
Patent number
US06787652B1

Reaction notes

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