Morpholine → 6-bromo-3-[(morpholin-4-yl)carbonyl]-1H-indazole

HRID 1398572Notes

Reaction equation

HRID 1398572 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=O)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:13])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 247280286-Bromo-1H-indazole-3-carboxylic acid

Product 1

HCID 681818546-bromo-3-[(morpholin-4-yl)carbonyl]-1H-indazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 6-bromo-1H-indazole-3-carboxylic acid (500 mg, 2.07 mmol) in DMF (10 mL) was added CDI (403.62 mg, 2.49 mmol) and the reaction mixture stirred at 45° C. for 40 minutes. Morpholine (0.36 ml, 4.16 mmol) was then added and the reaction mixture stirred at RT. The reaction mixture was quenched by diluting with water. The product was extracted into EtOAc (×2) and the combined organic extracts were then washed with water and brine and dried (Na2SO4), filtered and concentrated in vacuo to give the crude (78% pure) title compound: 1H NMR (500 MHz, DMSO) delta 3.58-3.79 (6H, m), 3.96-4.13 (2H, m), 7.36 (1H, dd, J=8.59, 1.66 Hz), 7.86 (1H, d, J=1.10 Hz), 7.93 (1H, s), 13.66 (1H, br. s.); LC-MS: m/z=+311.70 (M+H)+.

Workup

  1. stirringthe reaction mixture stirred at RT
  2. customThe reaction mixture was quenched
  3. additionby diluting with water
  4. extractionThe product was extracted into EtOAc (×2)
  5. washthe combined organic extracts were then washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a77fbb8c287432299f1dcd7d3ba975a
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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