Sodium Carbonate → HCID 135887207, compound

HRID 1627225Notes

Reaction equation

HRID 1627225 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9]([C:11]2[CH:15]=[C:14](Br)[N:13]([CH3:17])[N:12]=2)=[O:10])=[CH:3][CH:2]=1.C(OC([N:25]1[C:33]2[C:28](=[CH:29][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:32]=2)[CH:27]=[C:26]1[C:43]1[O:47][N:46]=[C:45]([CH3:48])[N:44]=1)=O)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9]([C:11]2[CH:15]=[C:14]([C:30]3[CH:29]=[C:28]4[C:33](=[CH:32][CH:31]=3)[NH:25][C:26]([C:43]3[O:47][N:46]=[C:45]([CH3:48])[N:44]=3)=[CH:27]4)[N:13]([CH3:17])[N:12]=2)=[O:10])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 56850539HCID 56850539, compoundHCID 58506151HCID 58506151, compound

Product 1

HCID 135887207HCID 135887207, compoundYield 16.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-Bromo-l-methyl-1H-pyrazole-3-carboxylic acid(pyridin-4-ylmethyl)-amide (90 mg, 0.3 mmol), and 2-(3-Methyl-1,2,4-oxadiazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole-1-carboxylic acid tert-butyl ester (142 mg, 0.33 mmol) in N,N dimethylformamide (1.5 ml) is added aqueous Na2CO3 (0.4 ml, 0.77 mmol). The mixture is purged with argon for 10 minutes. (Bis(di-t-butyl(4-dimethylaminutesophenyl)phosphine)dichloropalladium(II) (40 mg, 0.06 mmol), is then added and the reaction mixture is sealed in a seal tube and heated to 100° C. in a microwave reactor for 30 minutes. The reaction mixture is diluted with ethyl acetate (70 ml), washed with water (20 ml), brine (2×25 ml), dried over Na2SO4, filtered, and concentrated in vacuo. Purified by reverse phase LC/MS to provide the title compound 20 mg, (16%), LC/MS ESI m/z (M+H)+=414.9.

Workup

  1. customThe mixture is purged with argon for 10 minutes
  2. customthe reaction mixture is sealed in a seal tube
  3. washwashed with water (20 ml), brine (2×25 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurified by reverse phase LC/MS

Sources & evidence

ORD record
ord-172ef942ad374de4b52d7eae43f632ce
Source dataset
uspto-grants-2014_07
Patent number
US08785489B2

Reaction notes

Loading…