Sodium Carbonate → 2-{[(2,4-Difluorophenyl)methyl]oxy}-5-(1-methyl-1H-pyrazol-4-yl)-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamide

HRID 2204744Notes

Reaction equation

HRID 2204744 reaction equation
Br[C:2]1[C:3]([CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F: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].[CH3:34][N:35]1[CH:39]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH:37]=[N:36]1.C(=O)([O-])[O-].[Na+].[Na+]>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:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[CH2:18][O:17][C:5]1[CH:4]=[C:3]([CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:2]([C:38]2[CH:37]=[N:36][N:35]([CH3:34])[CH:39]=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]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 666119545-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamide

Product 1

HCID 666117642-{[(2,4-Difluorophenyl)methyl]oxy}-5-(1-methyl-1H-pyrazol-4-yl)-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamide (may be prepared as described in Example 9; 162 mg, 0.31 mmol) in 1,2-dimethoxyethane (5 ml) was added 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (78 mg, 0.38 mmol), Pd(Ph3P)4 (21.67 mg, 0.02 mmol) and sodium carbonate (0.63 ml, 0.63 mmol). The mixture was heated at 120° C. in the microwave for 35 minutes, cooled and the solvent removed in vacuo. Purification by MDAP yielded the title compound as a brown solid. 75 mg.

Workup

  1. temperaturecooled
  2. customthe solvent removed in vacuo
  3. customPurification by MDAP

Sources & evidence

ORD record
ord-bbcf66b2b2fe4f73865956d01e8b2807
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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