Cesium carbonate → HCID 117667207, compound

HRID 712608Notes

Reaction equation

HRID 712608 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.C([Sn](CCCC)(CCCC)[C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1)CCC.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:18]1[CH:19]=[CH:20][N:21]=[CH:22][C:17]=1[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27373162-(Tributylstannyl)pyrazineHCID 179301266-Bromo-1,2,3,4-tetrahydro-1,8-naphthyridine

Product 1

HCID 117667207HCID 117667207, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 21735183Dimethylformamide tolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-bromo-1,2,3,4-tetrahydro-[1,8]naphthyridine (350 mg, 1.6 mmol) in 14 mL of toluene/DMF 1:1 mixed solvents are added 2-tributylstannanyl-pyrazine (670 mg 1.8 mmol) and Cs2CO3 (1.6 g, 4.9 mmol). Then Pd(dppf)Cl2 (120 mg, 0.16 mmol) is added under N2 atmosphere. The mixture is heated at 110° C. for 16 hrs and the solvent is removed under vacuum. The residue is purified by flash column chromatography to give 190 mg of 6-pyrazin-2-yl-1,2,3,4-tetrahydro-[1,8]naphthyridine

Workup

  1. customthe solvent is removed under vacuum
  2. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-37a54f3249aa440e9ea3e87e172c24ed
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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