Sodium Carbonate → HCID 68989107, compound

HRID 240799Notes

Reaction equation

HRID 240799 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[CH:6]2)#[CH:2].I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].[N-:33]=[N+:34]=[N-:35].[Na+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CS(C)=O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:13]1([N:33]2[CH:2]=[C:1]([C:3]3[CH:4]=[C:5]4[C:9](=[CH:10][CH:11]=3)[NH:8][N:7]=[CH:6]4)[N:35]=[N:34]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

10

Reactant 6

HCID 10340Sodium CarbonateHCID 11575IodobenzeneHCID 33557Sodium AzideHCID 145742L-ProlineHCID 178424335-ethynyl-1H-indazoleHCID 23667548Sodium Ascorbate

Product 1

HCID 68989107HCID 68989107, compound

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent3×

Procedure

To a solution of Example 1C (30 mg, 0.21 mmol) in dimethyl sulfoxide (0.25 mL) was added iodobenzene (0.024 mL, 0.21 mmol), a solution of L-proline (5 mg, 0.042 mmol) and sodium carbonate (5 mg, 0.04 mmol) in water (0.1 mL), sodium azide (16 mg, 0.25 mmol), a solution of sodium ascorbate (8 mg, 0.04 mmol) in water (0.05 mL) and a solution of copper (II) sulfate pentahydrate (6 mg, 0.02 mmol) in water (0.05 mL) and the mixture was heated at 65° C. overnight. The mixture was centrifuged, and the crude solids were washed with methanol. The methanol wash was removed with a pipette. It was then dissolved in dimethyl sulfoxide and passed through a silica gel plug eluting with ethyl acetate. The product containing fractions were combined, concentrated in vacuo, and then treated with water. The mixture was centrifuged, and the solid was washed with water and methanol. The washes were removed with a pipette affording the title compound. 1H NMR (400 MHz,) δ ppm 13.17 (s, 1H), 9.28 (s, 1H), 8.34 (s, 1H), 8.17 (s, 1H), 7.96 (m, 3H), 7.65 (m, 3H), 7.52 (m, 1H). MS (ESI) m/z 262 (M+H).

Workup

  1. washthe crude solids were washed with methanol
  2. washThe methanol wash
  3. customwas removed with a pipette
  4. dissolutionIt was then dissolved in dimethyl sulfoxide
  5. washeluting with ethyl acetate
  6. additionThe product containing fractions
  7. concentrationconcentrated in vacuo
  8. additiontreated with water
  9. washthe solid was washed with water and methanol
  10. customThe washes were removed with a pipette

Sources & evidence

ORD record
ord-e022b8b118f6443688d530ec48696725
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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