Oxindole → HCID 178453008, compound

HRID 1615249Notes

Reaction equation

HRID 1615249 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH:11]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[C:16]2[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=O>C(O)C.N1CCCCC1>[O:10]=[C:2]1[NH:1][C:9]2[C:4](/[C:3]/1=[CH:11]\[C:13]1[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[C:16]3[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 2

HCID 321710OxindoleHCID 86651949HCID 86651949, compound

Product 1

HCID 178453008HCID 178453008, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of oxindole (13 mg, 0.01 mmol) and tert-butyl 5-formyl-1H-indazol-3-ylcarbamate (25 mg, 0.01 mmol) in ethanol (1 mL) was added piperidine (1 drop). The mixture was heated to 80° C. for 2 h and cooled to rt. The solution was loaded onto a silica gel column and the title compound was eluted with EtOAc/Hex 4:1 as a red solid (14 mg, 37%). 1H NMR (400 MHz, CD3OD) δ 8.14-8.02 (m, 2H), 7.90-7.83 (m, 2H), 7.63 (s, 1H), 7.24 (bs, 1H), 7.00-6.91 (m, 2H), 1.71 (s, 9H).

Workup

  1. temperaturecooled to rt
  2. washthe title compound was eluted with EtOAc/Hex 4:1 as a red solid (14 mg, 37%)

Sources & evidence

ORD record
ord-7ef115b11a8740b78b9f615bd9dae514
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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