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Potassium Carbonate → HCID 86305614, compound

HRID 712597
Notes
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Reaction equation

HRID 712597 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.[CH3:15][O:16][C:17]1[CH:18]=[N:19][CH:20]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:22]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([C:2]2[CH:3]=[C:4]3[C:9](=[N:10][CH:11]=2)[N:8]([C:12]([NH2:14])=[O:13])[CH2:7][CH2:6][CH2:5]3)[CH:20]=[N:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 38661613-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 117667602HCID 117667602, compound

Product 1

HCID 86305614HCID 86305614, compoundYield 36.1%

Reagents, catalysts & solvents 3

HCID 11714597
Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6-Bromo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (30 mg, 0.12 mmol), 3-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (43 mg, 0.18 mmol) and K2CO3 (32 mg, 0.23 mmol) are mixed in 1.0 mL of 1,4-dioxane and 0.10 mL of water. Argon gas is bubbled through the mixture for 10 min and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (8.3 mg, 0.01 mmol) is added. The mixture is heated at 100° C. for 2 hrs. Then solvents are removed and EtOAc (20 mL) is added. The mixture is filtered to remove any solid and the filtrate is concentrated to give the crude product. Purification by flash column chromatography affords 12.3 mg of the title product.

Workup

  1. customArgon gas is bubbled through the mixture for 10 min
  2. customThen solvents are removed
  3. additionEtOAc (20 mL) is added
  4. filtrationThe mixture is filtered
  5. customto remove any solid
  6. concentrationthe filtrate is concentrated
  7. customto give the crude product
  8. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-b310f6896a1d4af5a6c3e4b918b33bd0
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