Cesium carbonate → HCID 16118696, compound

HRID 1787591Notes

Reaction equation

HRID 1787591 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:16]=[N:15][C:14]([NH2:17])=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH:2]=1.Br[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:25][C:21]1[N:20]=[C:19]([NH:17][C:14]2[N:15]=[CH:16][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 792052-Bromo-6-methylpyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 68620238HCID 68620238, compound

Product 1

HCID 16118696HCID 16118696, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

5-Pyridin-3-yl-[1,7]naphthyridin-8-ylamine (0.1 g, 0.45 mmol) and 2-bromo-6-methylpyridine (0.14 g, 0.8 mmol) were dissolved in 4 ml dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (52 mg, 0.09 mmol), cesium carbonate (0.23 g, 0.72 mmol) and tri(dibenzylideneacetone)dipalladium chloroform complex (47 mg, 0.045 mmol) were added and the reaction mixture was stirred for 20 hrs at 130° C. The reaction mixture was then evaporated and purified by flash chromatography on silica gel (heptane/ethyl acetate 1:1->0:100 gradient). The desired product was obtained as a light yellow solid (66 mg, 47%), MS: m/e=314.0 (M+H+).

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurified by flash chromatography on silica gel (heptane/ethyl acetate 1:1->0:100 gradient)

Sources & evidence

ORD record
ord-ae19bdf49439425988639b55855b1245
Source dataset
uspto-grants-2009_03
Patent number
US07511055B2

Reaction notes

Loading…