Sodium Carbonate → HCID 86654745, compound

HRID 2092879Notes

Reaction equation

HRID 2092879 reaction equation
Cl[C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=3[O:22][CH3:23])[C:10]([CH3:12])([CH3:11])[C:6]=2[C:5]([F:25])=[C:4]([NH:26][C@@H:27]2[CH2:32][CH2:31][CH2:30][CH2:29][C@@H:28]2[NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:47][N:48]1[CH:52]=[C:51](B2OC(C)(C)C(C)(C)O2)[CH:50]=[N:49]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[CH3:23][O:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH2:13][N:9]1[C:10]([CH3:12])([CH3:11])[C:6]2[C:5]([F:25])=[C:4]([NH:26][C@@H:27]3[CH2:32][CH2:31][CH2:30][CH2:29][C@@H:28]3[NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:39])[CH3:37])[N:3]=[C:2]([C:51]3[CH:50]=[N:49][N:48]([CH3:47])[CH:52]=3)[C:7]=2[C:8]1=[O:24]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86654743HCID 86654743, compound

Product 1

HCID 86654745HCID 86654745, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

In a sealed tube, a mixture of tert-butyl (1S,2R)-2-(4-chloro-2-(2,4-dimethoxybenzyl)-7-fluoro-1,1-dimethyl-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (30 mg, 0.052 mmol), Na2CO3 aq (2M, 0.065 mL, 0.130 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (12.98 mg, 0.062 mmol), bis(triphenylphosphine)palladium chloride (3.65 mg, 5.20 μmol), and DMF (1 mL) was heated at 160° C. for 0.5 h in a microwave oven. The reaction mixture was then heated at 160° C. for an additional 4 h in a microwave oven and was subsequently purified by preparative HPLC to give the title compound as a light yellow solid (5 mg, 18%). [M+H] calc'd for C28H35FN6O3, 524. found 524.

Workup

  1. temperatureThe reaction mixture was then heated at 160° C. for an additional 4 h in a microwave oven
  2. customwas subsequently purified by preparative HPLC

Sources & evidence

ORD record
ord-ee4c56a24aca45e9b8f256ae96842afb
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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