Potassium Carbonate → HCID 117667315, compound

HRID 712593Notes

Reaction equation

HRID 712593 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=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>[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:2]2[CH:3]=[C:4]3[C:9](=[N:10][CH:11]=2)[NH:8][CH2:7][CH2:6][CH2:5]3)[CH:13]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 179301266-Bromo-1,2,3,4-tetrahydro-1,8-naphthyridine

Product 1

HCID 117667315HCID 117667315, compoundYield 61.5%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

6-Bromo-1,2,3,4-tetrahydro-[1,8]naphthyridine (243 mg, 1.1 mmol), 3-pyridinyl-boronic acid (168 mg, 1.4 mmol) and K2CO3 (315 mg, 2.3 mmol) are mixed in 3.0 mL of 1,4-dioxane and 0.30 mL of water. Argon gas is bubbled through the mixture for 10 min and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (81 mg, 0.11 mmol) is added. The mixture is heated at 100° C. for 16 hrs. Then solvents are removed and EtOAc (50 mL) is added along with 30 mL of water. The mixture is filtered to remove any solid and the organic layer is separated. The aqueous layer is extracted with EtOAc (2×25 mL) and the organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 143 mg of 6-Pyridin-3-yl-1,2,3,4-tetrahydro-[1,8]naphthyridine

Workup

  1. customArgon gas is bubbled through the mixture for 10 min
  2. customThen solvents are removed
  3. additionEtOAc (50 mL) is added along with 30 mL of water
  4. filtrationThe mixture is filtered
  5. customto remove any solid
  6. customthe organic layer is separated
  7. extractionThe aqueous layer is extracted with EtOAc (2×25 mL)
  8. concentrationconcentrated
  9. customto give the crude product
  10. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-51b3c018303248b78976cd987a8ea1ac
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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