Acetic Acid → HCID 178497392, compound

HRID 218455Notes

Reaction equation

HRID 218455 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[CH:14]=O)=[O:4].CC(O)=O.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[CH2:14][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8083MorpholineHCID 178497393HCID 178497393, compound

Product 1

HCID 178497392HCID 178497392, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-formyl-1H-indazole-5-carboxylic acid methyl ester (600 mg, 2.94 mmol) in DCM was added HOAc (0.25 mL, 4.41 mmol) followed by morpholine (0.31 mL, 3.53 mmol) and NaHB(OAc)3 (809.6 mg, 3.62 mmol) at rt. The reaction was stirred at rt overnight, and was quenched with brine. The reaction mixture was extracted with EtOAc, washed with brine, dried, and concentrated in vacuo. Purification by flash column afforded 3-(4-morpholinylmethyl)-1H-indazole-5-carboxylic acid methyl ester (800 mg, 95.7%).

Workup

  1. customwas quenched with brine
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column

Sources & evidence

ORD record
ord-fc3ed67f76d244058ef7aa50b8f80a84
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

Loading…