Cesium carbonate → HCID 57815279, compound

HRID 84864Notes

Reaction equation

HRID 84864 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[CH:7][CH:6]=2.[C:12](=[O:19])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[NH2:13].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:4]1[C:5]2[C:10](=[N:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([NH:13][C:12](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 128788183-Bromo-1,5-naphthyridine

Product 1

HCID 57815279HCID 57815279, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

Commercial 3-bromo-[1,5]naphthyridine (1.00 g, 4.8 mmol) was dissolved in 50 mL dioxane. To it were added t-butyl carbamate (0.85 g, 7.2 mmol), cesium carbonate (3.13 g, 9.6 mmol), Pd2(dba)3 (0.22 g, 0.24 mmol) and XantPhos (0.42 g, 0.72 mmol). The mixture was degassed with Ar stream and stirred under Ar in 85° C. bath for 5 h. The mixture was concentrated, taken into 400 mL EtOAc and 200 mL water. The organic phase was separated, dried, concentrated and subjected to flash column (0-30% EtOAc in DCM) to obtain tert-butyl 1,5-naphthyridin-3-ylcarbamate (1.04 g, 88% yield). This compound was treated with 50 mL 4N HCl in dioxane for overnight. To the suspension was poured diethyl ether 300 mL. The suspension was vigorously stirred. The solid product was collected by filtration as 1,5-naphthyridin-3-amine di-HCl salt.

Workup

  1. customThe mixture was degassed with Ar stream
  2. concentrationThe mixture was concentrated
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3597577f24247549732f23f876e4d53
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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