Cesium carbonate → HCID 46203867, compound

HRID 1724871Notes

Reaction equation

HRID 1724871 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[C:4]([C:9]2[N:14]=[C:13]3[N:15]=[CH:16][CH:17]=[C:18]([NH2:19])[C:12]3=[N:11][CH:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+].N[C:29]1[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:32]=[CH:31][N:30]=1.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].O>[F:21][C:2]([F:1])([F:20])[C:3]1[C:4]([C:9]2[N:14]=[C:13]3[N:15]=[CH:16][CH:17]=[C:18]([NH:19][C:31]4[CH:32]=[CH:33][C:34]([C:35]([F:38])([F:37])[F:36])=[CH:29][N:30]=4)[C:12]3=[N:11][CH:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27609202-Amino-3-(trifluoromethyl)pyridineHCID 46203865HCID 46203865, compound

Product 1

HCID 46203867HCID 46203867, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a de-gassed mixture of 3-[3-(trifluoromethyl)pyridin-2-yl]pyrido[2,3-b]pyrazin-8-amine (72 mg, 0.25 mmol), cesium carbonate (162 mg, 0.5 mmol), 2-amino-trifluoromethyl pyridine (45 mg, 0.25 mmol) in dioxane (5 mL) under nitrogen, add Pd2dba3 (11 mg) and xantphos (7 mg). Stir the mixture at 100° C. for 3 hours, cool, add water (10 mL) and extract with EtOAc. Dry over Na2SO4, concentrate under vacuum. Purify by chromatography eluting with dichloromethane/methanol/ammonium hydroxide mixture to give the title compound. MS 437 (M+1). 1H NMR δ (CDCl3) 9.42 (1H, s), 9.28 (1H, s), 9.11 (1H, d), 8.95 (1H, d), 8.90 (1H, d), 8.72 (1H, s), 8.25 (1H, d), 7.89 (1H, d), 7.61 (1H,dd), 7.13 (1H, d).

Workup

  1. temperaturecool
  2. extractionextract with EtOAc
  3. dry with materialDry over Na2SO4
  4. concentrationconcentrate under vacuum
  5. customPurify by chromatography
  6. washeluting with dichloromethane/methanol/ammonium hydroxide mixture

Sources & evidence

ORD record
ord-030d6d119f7e400786c9dad8b09293e5
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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