Sodium Carbonate → HCID 69936744, compound

HRID 1623854Notes

Reaction equation

HRID 1623854 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:23]1[CH:24]=[CH:25][C:26]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:41]=2[F:47])=[C:27]([CH:37]=1)[C:28]([NH:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)=[O:29]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:47][C:41]1[CH:42]=[C:43]([F:46])[CH:44]=[CH:45][C:40]=1[CH2:39][O:38][C:26]1[CH:25]=[CH:24][C:23]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)=[CH:37][C:27]=1[C:28]([NH:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)=[O:29]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67106849HCID 67106849, compound

Product 1

HCID 69936744HCID 69936744, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (112 mg, 0.54 mmol), tetrakis(triphenylphosphine)palladium(0) (24.81 mg, 0.02 mmol) and sodium carbonate (0.72 ml, 0.72 mmol) were added to a solution of 5-bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-N-3-pyridinylbenzamide (may be prepared by Example 81; 150 mg, 0.36 mmol) in 1,2-dimethoxyethane (3 ml), and the mixture was heated to 120° C. for 1 hr under microwave conditions. The mixture was evaporated under reduced pressure and the residue was purified by MDAP to yield the title compound. 58 mg.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue was purified by MDAP

Sources & evidence

ORD record
ord-f54153fc873b428c9967bffe80f04ee8
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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