Cesium carbonate → HCID 16118825, compound

HRID 1787596Notes

Reaction equation

HRID 1787596 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[N:16][C:15]([NH2:18])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[N:13]3)[CH:5]=[N:6][CH:7]=1.Br[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=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>[F:26][C:23]1[CH:24]=[CH:25][C:20]([NH:18][C:15]2[N:16]=[CH:17][C:8]([C:4]3[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[C:9]3[C:14]=2[N:13]=[CH:12][CH:11]=[CH:10]3)=[N:21][CH:22]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27831712-Bromo-5-fluoropyridineHCID 68621638HCID 68621638, compound

Product 1

HCID 16118825HCID 16118825, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

5-(5-Fluoro-pyridin-3-yl)-[1,7]naphthyridin-8-ylamine (0.1 g, 0.42 mmol) and 2-bromo-5-fluoropyridine (0.13 g, 0.76 mmol) (Example C) were dissolved in 3 ml dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (48 mg, 0.084 mmol), cesium carbonate (0.22 g, 0.67 mmol) and tri(dibenzylideneacetone)dipalladium chloroform complex (43 mg, 0.042 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 95:5->30:70 gradient). The desired product was obtained as a light red solid (35 mg, 25%), MS: m/e=336.3 (M+H+).

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurified by flash chromatography on silica gel (heptane/ethyl acetate 95:5->30:70 gradient)

Sources & evidence

ORD record
ord-33d16f82fb564435b4fa14d04e61ec2a
Source dataset
uspto-grants-2009_03
Patent number
US07511055B2

Reaction notes

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