Dichloromethane → HCID 86305761, compound

HRID 712613Notes

Reaction equation

HRID 712613 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[C:15](=[N:16][CH:17]=1)[N:14]([C:18]([NH2:20])=[O:19])[CH2:13][CH2:12][CH2:11]2.[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:7]=[CH:6][N:5]=[CH:4][C:3]=2[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:24][CH:23]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 117667632HCID 117667632, compound

Product 1

HCID 86305761HCID 86305761, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6-(4-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 1.0 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 3.5 hrs and then it is cooled down to room temperature. 30 mL of DCM and 20 mL of water are added and the organic layer is separated. The aqueous layer is extracted with DCM (2×20 mL) and all the organic layers are combined, dried and concentrated to give crude product. Purification by flash column chromatography affords 39 mg of the titled compound.

Workup

  1. customThe Argon gas is bubbled through the solution for 5 min
  2. temperatureit is cooled down to room temperature
  3. customthe organic layer is separated
  4. extractionThe aqueous layer is extracted with DCM (2×20 mL) and all the organic layers
  5. customdried
  6. concentrationconcentrated
  7. customto give crude product
  8. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-174b3fd2ff714dbca02488e0bae3ac41
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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