Cesium carbonate → HCID 9909873, compound

HRID 396160Notes

Reaction equation

HRID 396160 reaction equation
Br[C:2]1[N:6]2[C:7]([CH3:17])=[N:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]2=[N:4][C:3]=1[O:18][CH2:19][C:20]1[N:21]([CH2:25][CH3:26])[N:22]=[CH:23][N:24]=1.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>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]>[CH2:25]([N:21]1[C:20]([CH2:19][O:18][C:3]2[N:4]=[C:5]3[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:9][N:8]=[C:7]([CH3:17])[N:6]3[C:2]=2[C:28]2[S:27][CH:31]=[CH:30][CH:29]=2)=[N:24][CH:23]=[N:22]1)[CH3:26]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27339602-Thiopheneboronic acidHCID 23003182HCID 23003182, compound

Product 1

HCID 9909873HCID 9909873, compoundYield 14.7%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of 3-bromo-2-(2-ethyl-2H-[1,2,4]triazol-3-ylmethoxy)-5-methyl-8-phenylimidazo[1,2-d][1,2,4]triazine (70 mg, 0.169 mmol), 2-thiopheneboronic acid (32 mg, 0.254 mmol) and cesium carbonate (110 mg, 0.338 mmol) in anhydrous 1,4-dioxane (5 ml) was degassed using three freeze-pump-thaw cycles. Tris(dibenzylideneacetone)dipalladium(0) (15.5 mg, 0.017 mmol) and a 0.1M solution of tri-tert-butylphosphine in 1,4-dioxane (0.406 ml, 0.406 mmol) was added, and the mixture was further degassed with two more freeze-pump-thaw cycles before heating at 90° C. under nitrogen for 17 h. The mixture was filtered through glass fibre paper, washed with ethyl acetate. The filtrate was washed with saturated NaCl solution, separated, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 2% MeOH in CH2Cl2), and the product recrystallised from CH2Cl2 to afford the title compound (10.4 mg) as a white solid. δH (400 MHz; CDCl3) 1.28 (3H, t, J 7.2), 2.58 (3H, d), 4.19 (2H, q, J 7.2), 5.68 (2H, s), 7.18 (2H, m), 7.57 (4H, m), 7.89 (1H, s), 8.61 (2H, m); m/z (ES+) 414/416 (M++H).

Workup

  1. customwas degassed
  2. customthe mixture was further degassed with two more freeze-pump-thaw cycles
  3. filtrationThe mixture was filtered through glass fibre paper
  4. washwashed with ethyl acetate
  5. washThe filtrate was washed with saturated NaCl solution
  6. customseparated
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo
  9. customThe residue was purified by flash chromatography (SiO2; 2% MeOH in CH2Cl2)
  10. customthe product recrystallised from CH2Cl2

Sources & evidence

ORD record
ord-0fe627677bad4521a90f0759b4170445
Source dataset
uspto-grants-2003_08
Patent number
US06608062B1

Reaction notes

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