Bromine → HCID 178468688, compound

HRID 530835Notes

Reaction equation

HRID 530835 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.[Br:16]Br.C(OCC)(=O)C.CCCCCC>C(O)C>[Br:16][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=2)[NH:2][N:3]=1

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 21226206Ethyl acetate hexaneHCID 67984756ethyl 1H-indazole-5-carboxylate hydrochloride

Product 1

HCID 178468688HCID 178468688, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

ethyl 1H-indazole-5-carboxylate hydrochloride (146 g, 0.645 mol) was dissolved in ethanol (4 L, anhydrous). Bromine (113.3 g, 0.709 mol) in 200 ethanol was added at room temperature. The reaction mixture was allowed to stir for 17 hours at room temperature. TLC (30% ethyl acetate/hexane) indicated that starting material was left. Bromine (40 g in 100 mL of ethanol) was added at room temperature. After 1 hour, TLC indicated no starting material was left. Ethanol was evaporated (2 L removed) and the mixture was poured into ice-water (8 L). The purple solid was stirred and 750 mL of saturated Na2S2O3 and NaOH solution was added to adjust the pH to 10-11. Total volume was 10 L. The mixture was stirred for 30 minutes and the solid were filtered and washed with 1.5 L of water and dried in a vacuum oven to obtain 170 gram of product as yellow solid.

Workup

  1. waitwas left
  2. waitAfter 1 hour
  3. waitwas left
  4. customEthanol was evaporated
  5. custom(2 L removed)
  6. additionthe mixture was poured into ice-water (8 L)
  7. stirringThe purple solid was stirred
  8. addition750 mL of saturated Na2S2O3 and NaOH solution was added
  9. stirringThe mixture was stirred for 30 minutes
  10. filtrationthe solid were filtered
  11. washwashed with 1.5 L of water
  12. customdried in a vacuum oven

Sources & evidence

ORD record
ord-36eb59c71bf74da797faef65fe8d24d8
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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