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Dichloromethane → HCID 86305757, compound

HRID 712611
Notes
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Reaction equation

HRID 712611 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[N:16][CH:17]=2)[N:14]([C:18]([NH2:20])=[O:19])[CH2:13][CH2:12][CH2:11]3)[CH:5]=[N:6][CH:7]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>O1CCOCC1.O>[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:3]=[C:4]([C:8]3[CH:9]=[C:10]4[C:15](=[N:16][CH:17]=3)[N:14]([C:18]([NH2:20])=[O:19])[CH2:13][CH2:12][CH2:11]4)[CH:5]=[N:6][CH:7]=2)=[CH:24][CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 117667498HCID 117667498, compound

Product 1

HCID 86305757HCID 86305757, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6-(5-Bromo-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (50 mg, 0.15 mmol), 4-fluorophenylboronic acid (42 mg, 0.30 mmol) and 2.0 M Na2CO3 aqueous solution (0.15 mL, 0.30 mmol) are dissolved in 2.0 mL of 1,4-dioxane. The Argon gas is bubbled through the solution for 5 min. Then PdCl2dppf (7.7 mg, 0.011 mmol) is added. The mixture is heated at 100° C. for 2 hrs before it is cooled down to room temperature. Then 30 mL of DCM and 20 mL of water are added. The organic layer is separated and the aqueous layer is extracted with DCM (2×20 mL). All the organic layers are combined, dried and concentrated to give crude product. Purification by flash column chromatography followed by washing with EtOAc (2×1 mL) affords 35 mg of the titled product.

Workup

  1. customThe Argon gas is bubbled through the solution for 5 min
  2. temperatureis cooled down to room temperature
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is extracted with DCM (2×20 mL)
  5. customdried
  6. concentrationconcentrated
  7. customto give crude product
  8. customPurification by flash column chromatography
  9. washby washing with EtOAc (2×1 mL)

Sources & evidence

ORD record
ord-e180c7b331dd44758716a2c5b15595cf
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