Sodium Carbonate → HCID 11612384, compound

HRID 1818862Notes

Reaction equation

HRID 1818862 reaction equation
[OH:1][CH:2]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1)[CH:3]([CH2:7][CH2:8][N:9]1[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH3:16])[C:10]1=[O:17])[C:4]([OH:6])=[O:5].[C:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)(=[O:29])[CH3:28].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.[Pd]>[C:27]([C:30]1[CH:35]=[CH:34][C:33]([C:23]2[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][CH:2]([OH:1])[CH:3]([CH2:7][CH2:8][N:9]3[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH3:16])[C:10]3=[O:17])[C:4]([OH:6])=[O:5])=[CH:21][CH:22]=2)=[CH:32][CH:31]=1)(=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 37021224-Acetylphenylboronic acidHCID 57887030HCID 57887030, compound

Product 1

HCID 11612384HCID 11612384, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 3-hydroxy-5-(4-iodophenyl)-2-[2-(3-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)ethyl]pentanoic acid (10 mg, 21 μmol) in dimethylformamide (0.5 mL) was added in one portion to a mixture of p-acetylbenzeneboronic acid (4.0 mg, 25 μmol) and fibrecat FC1001 (2.71% Pd; 8.3 mg, 2.0 μmol) in a Smith microwave reaction vial. Aqueous sodium carbonate solution (1.0 M; 53 μL, 53 μmol) was added and the vial capped. The crude reaction mixture was heated at 150° C. for 15 min using a Smith Synthesiser microwave reactor. On cooling the vial was opened and the contents filtered through a Whatman 5 μM filter tube, washing the filter cake with methanol (2×1 mL). The filtrate was evaporated and the resulting residue was purified using mass directed auto-preparative reverse phase HPLC to give the title compound (6.0 mg, 61%) as a white solid. LC/MS: 2.82 min; z/e 465, calcd (M+1) 465. H NMR (400 MHz: DMSO-d6): 8.00 (2H), 7.80 (2H), 7.60 (4H), 7.30 (2H), 6.65 (1H), 3.70 (3H), 3.10 (3H), 2.80 (1H), 2.60 (2H), 2.30 (1H), 1.85 (2H), 1.60 (1H).

Workup

  1. customThe crude reaction mixture
  2. temperatureOn cooling the
  3. filtrationthe contents filtered through a Whatman 5 μM
  4. filtrationfilter tube
  5. washwashing the filter cake with methanol (2×1 mL)
  6. customThe filtrate was evaporated
  7. customthe resulting residue was purified

Sources & evidence

ORD record
ord-63c278d96f774618804a108088d808f0
Source dataset
uspto-grants-2009_10
Patent number
US07601729B2

Reaction notes

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