Cesium carbonate → HCID 59276196, compound

HRID 2070885Notes

Reaction equation

HRID 2070885 reaction equation
Br[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.BrC1N2N=C(N)N=C2C=CC=1.IC1C=CC(C#N)=CC=1.C(=O)([O-])[O-:41].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)[C:53]2[C:66]3[O:65]C4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)[C:57]=3[CH:56]=[CH:55][CH:54]=2)C=CC=CC=1.O.[Cl-].[Na+].O>O1CCOCC1>[OH:65][C:66]1[CH:53]=[C:54]([C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:12]4[CH:19]=[CH:18][C:15]([C:16]([NH2:17])=[O:41])=[CH:14][CH:13]=4)[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH:55]=[CH:56][CH:57]=1

Participants

8

Reactant 6

HCID 10796Cesium carbonateHCID 764674-IodobenzonitrileHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23713072Sodium chloride dihydrateHCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amineHCID 86640816HCID 86640816, compound

Product 1

HCID 59276196HCID 59276196, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzonitrile. To an orange solution of 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (2.00 g, 9.39 mmol) in dioxane (100 mL) was added 4-iodobenzonitrile (4.30 g, 18.78 mmol), cesium carbonate (6.12 g, 18.78 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (1.086 g, 1.878 mmol) and tris(dibezylideneacetone)palladium (0.903 g, 0.986 mmol) at room temperature under nitrogen. The reaction mixture was heated at 100° C. for 18 h under nitrogen. Upon completion of the reaction, as indicated by LCMS, the reaction mixture was poured into water/brine, and extracted with ethyl acetate several times. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. The crude mixture was triturated with ethyl acetate to give the title compound as a brownish yellow solid (0.565 g, 20% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 10.55 (s, 1H), 7.89-7.87 (m, 2H), 7.77-7.75 (m, 2H), 7.71-7.69 (m, 1H), 7.58-7.54 (m, 1H), 7.49-7.46 (m, 1H); MS (ESI) m/z 315.14 [M+1]+

Workup

  1. customUpon completion of the reaction
  2. extractionextracted with ethyl acetate several times
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude mixture was triturated with ethyl acetate

Sources & evidence

ORD record
ord-2017501b0b744f9888b3d12e2ecbf281
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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