Pyridine → HCID 19081257, compound

HRID 963502Notes

Reaction equation

HRID 963502 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:19]>O1CCCC1>[NH:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:18](=[O:19])[O:20][C:21]3[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=3)[CH:10]=2)[CH:6]=[N:7]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 814231H-Indazol-6-amineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 19081257HCID 19081257, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 6-amino-1H-indazole (2.00 g) and pyridine (2.67 ml) in tetrahydrofuran was stirred at 0° C. and then p-nitrophenyl chloroformate (3.18 g) was added and stirred at the same temperature for 2 hours. The reaction mixture was evaporated and partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over sodium sulfate, and evaporated in vacuo. The pale yellow powder was washed with isopropyl ether and diethyl ether, and vacuumed to afford 4-nitrophenyl N-(lH-indazol-6-yl)carbamate (2.67 g).

Workup

  1. stirringstirred at the same temperature for 2 hours
  2. customThe reaction mixture was evaporated
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. washThe pale yellow powder was washed with isopropyl ether and diethyl ether

Sources & evidence

ORD record
ord-4f06a370f52243bfbc9037d4bcff16bf
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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