Cesium carbonate → HCID 58318784, compound

HRID 2401507Notes

Reaction equation

HRID 2401507 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[NH2:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13].C([O-])([O-])=O.[Cs+].[Cs+].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>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].O1CCOCC1>[N:4]1[CH:3]=[C:2]([NH:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[CH:7]=[N:6][CH:5]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 167023-AminobenzonitrileHCID 783445-BromopyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 58318784HCID 58318784, compoundYield 93.4%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

5-Bromopyrimidine (1 g, 6 mmol, 1 eq), 3-aminobenzonitrile (0.892 mg, 7.55 mol, 1.20 eq), Cs2CO3 (2.87 g, 8.81 mmol, 1.40 eq), Pd2(dba)3 (347 mg, 0.603 mmol, 0.080 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (437 mg, 0.755 mmol, 0.120 eq) and dioxane (15 mL) were added to a microwave vial. The vial was purged with argon, capped and heated at 100° C. for 18 h. After cooling the reaction was filtered over a plug of celite and the plug was washed with 5% MeOH/CH2Cl2. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 1.1 g (89%) of the title compound as an orange solid: 1H NMR (400 MHz, CDCl3) δ 8.86 (s, 1H), 8.73 (s, 1H), 8.63 (s, 2H), 7.49-7.43 (m, 2H), 7.43-7.39 (m, 1H), 7.32 (dt, J=7.2, 1.4 Hz, 1H); [M+1]+: 197.2.

Workup

  1. customThe vial was purged with argon
  2. customcapped
  3. temperatureAfter cooling the reaction
  4. filtrationwas filtered over a plug of celite
  5. washthe plug was washed with 5% MeOH/CH2Cl2
  6. customThe solvents were removed in vacuo
  7. customthe crude mixture was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-ff8098b61beb428f9005e76644ed1a53
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

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