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Sodium Carbonate → HCID 86305860, compound

HRID 712694
Notes
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Reaction equation

HRID 712694 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([C:12]([NH2:14])=[O:13])[CH2:7][CH2:6][CH2:5]2.[N:15]1([C:20]([C:22]2[CH:23]=[N:24][CH:25]=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:27]=2)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[N:15]1([C:20]([C:22]2[CH:27]=[C:26]([C:2]3[CH:3]=[C:4]4[C:9](=[N:10][CH:11]=3)[N:8]([C:12]([NH2:14])=[O:13])[CH2:7][CH2:6][CH2:5]4)[CH:25]=[N:24][CH:23]=2)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 53217185(Pyrrolidin-1-yl)[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]methanoneHCID 117667602HCID 117667602, compound

Product 1

HCID 86305860HCID 86305860, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 6-bromo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (55 mg, 0.22 mmol) and pyrrolidin-1-yl-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-methanone (78 mg, 0.26 mmol) in 1,4-dioxane (2 mL) is added 2.0 N aqueous sodium carbonate solution (0.23 mL, 0.46 mmol). Argon gas is bubbled through the solution for 5 min. To the mixture is added PdCl2(dppf) catalyst (12 mg, 0.02 mmmol) in one portion. The mixture is heated at 90° C. for 2 hrs. The mixture is filtered through short pad of diatomaceous earth, rinsing with EtOAC (3×1 mL). The filtrate is dried under reduced pressure. The reaction mixture is purified by Mass-triggered reverse phase HPLC to give 36 mg of the titled product.

Workup

  1. customArgon gas is bubbled through the solution for 5 min
  2. additionTo the mixture is added PdCl2(dppf) catalyst (12 mg, 0.02 mmmol) in one portion
  3. filtrationThe mixture is filtered through short pad of diatomaceous earth
  4. washrinsing with EtOAC (3×1 mL)
  5. customThe filtrate is dried under reduced pressure
  6. customThe reaction mixture is purified by Mass-triggered reverse phase HPLC

Sources & evidence

ORD record
ord-30cb3a191b9d48a7bb9aaad57373c820
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181272B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes