Water → HCID 178473417, compound

HRID 880943Notes

Reaction equation

HRID 880943 reaction equation
[OH:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[NH:4][N:3]=1.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].O>N1C=CC=CC=1>[OH:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[N:4]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10928Ethyl chloroformate2×HCID 178497397HCID 178497397, compound

Product 1

HCID 178473417HCID 178473417, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 3-hydroxy-1H-indazole-5-carboxylate (1.60 g, 8.33 mmol) was suspended in pyridine (10 mL). Ethyl chloroformate (0.90 mL, 9.3 mmol) was added slowly and the reaction was stirred at room temperature for 1 hour. Additional ethyl chloroformate (0.30 mL, 3.1 mmol) was added and the reaction was stirred for another 30 minutes. The reaction was poured into water (65 mL) and cooled in a refrigerator for 3 hours. The brown solid was collected by filtration, rinsed with water, and dried under vacuum to give the title compound (1.75 g, 80%). +ESI (M+H) 265.1; 1H NMR (400 MHz, CDCl3, δ): 8.56 (s, 1H), 8.29 (d, J=7.8 Hz, 1H), 8.13 (br. s., 1H), 4.59 (q, J=7.0 Hz, 2H), 3.97 (s, 3H), 1.56 (t, J=7.0 Hz, 3H).

Workup

  1. stirringthe reaction was stirred for another 30 minutes
  2. temperaturecooled in a refrigerator for 3 hours
  3. filtrationThe brown solid was collected by filtration
  4. washrinsed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2db167ed5dcd4820ae1c010520598f58
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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