HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Carbonate → 2-[(Phenylmethyl)oxy]-N,5-di-3-pyridinylbenzamide

HRID 1623839
Notes
Print preview

Reaction equation

HRID 1623839 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].C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)O1>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:39]3[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=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 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 369825032-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

Product 1

HCID 699364502-[(Phenylmethyl)oxy]-N,5-di-3-pyridinylbenzamide

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

To a microwave vial was added 5-bromo-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in example 2; 200 mg, 0.52 mmol), 1,4-dioxane (2 ml), 1M sodium carbonate (1.04 ml, 1.04 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (107 mg, 0.52 mmol) and tetrakis(triphenylphosphine)palladium(0) (36.2 mg, 0.03 mmol). The vial was sealed and heated to 100° C. for 30 min under microwave conditions. The mixture was evaporated under reduced pressure and the residue was purified using the MDAP. Some impurities persisted and the mixture was re-purified using MDAP to yield the title compound. 17 mg.

Workup

  1. customThe vial was sealed
  2. customThe mixture was evaporated under reduced pressure
  3. customthe residue was purified
  4. customthe mixture was re-purified

Sources & evidence

ORD record
ord-ee60d0558fa54219be4e68ea742858a1
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778939B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes