Sodium Carbonate → HCID 69936703, compound

HRID 1623851Notes

Reaction equation

HRID 1623851 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8].[CH3:27][N:28]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[N:29]1.C(=O)([O-])[O-].[Na+].[Na+]>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.COCCOC>[C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][O:17][C:5]1[CH:4]=[CH:3][C:2]([C:31]2[CH:30]=[N:29][N:28]([CH3:27])[CH:32]=2)=[CH:16][C:6]=1[C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8])#[N:26]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67108054HCID 67108054, compound

Product 1

HCID 69936703HCID 69936703, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave vial was added 5-bromo-2-{[(2-cyanophenyl)methyl]oxy}-N-3-pyridinylbenzamide (may be prepared as described in example 23; 172 mg, 0.42 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (96 mg, 0.46 mmol), 1,2-dimethoxyethane (2 ml), 1M sodium carbonate (0.84 ml, 0.84 mmol) and tetrakis(triphenylphosphine)palladium(0) (29.2 mg, 0.025 mmol). The vial was sealed and heated to 120° C. for 1 hr under microwave conditions. The mixture was evaporated under reduced pressure. Water (5 ml) was added to the residue and the mixture was extracted with ethyl acetate (3×10 ml). The organics were combined, evaporated under reduced pressure and the residue was purified using MDAP to yield the title compound. 58 mg.

Workup

  1. customThe vial was sealed
  2. customThe mixture was evaporated under reduced pressure
  3. additionWater (5 ml) was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate (3×10 ml)
  5. customevaporated under reduced pressure
  6. customthe residue was purified

Sources & evidence

ORD record
ord-15e1a86c256746f19d8b854728fab05b
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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