Sodium Ascorbate → HCID 86635703, compound

HRID 598909Notes

Reaction equation

HRID 598909 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)=[N+:2]=[N-:3].[F:13][C:14]([F:36])([F:35])[C:15]1[N:20]=[CH:19][C:18]([CH2:21][C@H:22]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:23][CH2:24][C:25]#[CH:26])=[CH:17][CH:16]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.[O-]S([O-])(=O)=O.[Cu+2]>[NH:9]1[C:10]2[C:6](=[CH:5][C:4]([N:1]3[CH:26]=[C:25]([CH2:24][CH2:23][C@@H:22]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[CH2:21][C:18]4[CH:19]=[N:20][C:15]([C:14]([F:13])([F:36])[F:35])=[CH:16][CH:17]=4)[N:3]=[N:2]3)=[CH:12][CH:11]=2)[CH:7]=[N:8]1

Participants

6

Reactant 3

HCID 23667548Sodium AscorbateHCID 57950691HCID 57950691, compoundHCID 86635702HCID 86635702, compound

Product 1

HCID 86635703HCID 86635703, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

A mixture of 5-azido-1H-indazole (126 mg, 789 μmol), (R)-tert-butyl 1-(6-(trifluoromethyl)pyridin-3-yl)hex-5-yn-2-ylcarbamate (270 mg, 789 μmol), CuSO4 (6.3 mg, 39 μmol), and sodium ascorbate (16 mg, 79 μmol) in t-BuOH/H2O (1:1, 2 mL) was stirred at room temperature for 8 hours. The mixture was partitioned between saturated aqueous NaCO3 (15 mL) and DCM (15 ml). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×15 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting yellow solid was dissolved in MeOH/DCM, absorbed onto silica gel, and purified by flash chromatography (silica gel, 3% to 8% MeOH/DCM) to deliver tert-butyl(R)-4-(1-(1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl)-1-(6-(trifluoromethyl)pyridin-3-yl)butan-2-ylcarbamate (85 mg, 21%) as a light yellow solid. LCMS (API-ES) m/z: 502.1 (M+H+).

Workup

  1. customThe mixture was partitioned between saturated aqueous NaCO3 (15 mL) and DCM (15 ml)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×15 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting yellow solid was dissolved in MeOH/DCM
  7. customabsorbed onto silica gel
  8. custompurified by flash chromatography (silica gel, 3% to 8% MeOH/DCM)

Sources & evidence

ORD record
ord-34cb96d67b824c7490a23d84162a44de
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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