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Sodium Carbonate → 2-[(Phenylmethyl)oxy]-5-(1H-pyrazol-4-yl)-N-3-pyridinylbenzamide

HRID 1623837
Notes
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Reaction equation

HRID 1623837 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][CH:20]=2)=[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].CC1(C)C(C)(C)OB([C:33]2[CH:34]=[N:35][N:36](C(OC(C)(C)C)=O)[CH:37]=2)O1.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.O1CCOCC1>[C:19]1([CH2:18][O:17][C:5]2[CH:4]=[CH:3][C:2]([C:33]3[CH:34]=[N:35][NH:36][CH:37]=3)=[CH:16][C:6]=2[C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:8])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 369825032-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

Product 1

HCID 671080462-[(Phenylmethyl)oxy]-5-(1H-pyrazol-4-yl)-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave vial was added 5-bromo-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in example 2; 310 mg, 0.81 mmol), 1,1-dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (262 mg, 0.89 mmol), 1,4-dioxane (3 ml), sodium carbonate (1.62 ml, 1.62 mmol) and tetrakis(triphenylphosphine)palladium(0) (56.1 mg, 0.05 mmol). The vial was sealed and heated to 120° C. for 25 min under microwave conditions. The mixture was evaporated under reduced pressure and water (5 ml) was added to the residue. The mixture was extracted with ethyl acetate (3×10 ml). The organics were combined and evaporated under reduced pressure, and the residue was purified using the MDAP to yield the title compound. 44 mg.

Workup

  1. customThe vial was sealed
  2. customThe mixture was evaporated under reduced pressure and water (5 ml)
  3. additionwas 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-4a2b9882de1c4a57881199719b749b31
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778939B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes