Dimethylamine → 6-bromo-N,N-dimethyl-1H-indazole-3-carboxamide

HRID 1398569Notes

Reaction equation

HRID 1398569 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.C[CH2:15][N:16]=[C:17]=NCCCN(C)C.Cl.CNC.C1COCC1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:16]([CH3:17])[CH3:15])=[O:13])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 247280286-Bromo-1H-indazole-3-carboxylic acid

Product 1

HCID 681815956-bromo-N,N-dimethyl-1H-indazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-bromo-1H-indazole-3-carboxylic acid (1 g, 4.15 mmol) and EDC.HCl (1.2 g, 6.2 mmol) in DMF (5 mL) was added 2 M dimethylamine in THF (3.45 mL, 10.3 mmol). Mixture was stirred at RT overnight. The reaction mixture was concentrated in vacuo to remove the volatiles, then diluted with EtOAc (30 mL) and washed with water. The aqueous layer was extracted with more EtOAc (20 mL). The combined organics were washed with water (30 mL), dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a white solid: 1H NMR (250 MHz, DMSO) delta 3.06 (3H, s), 7.34 (1H, dd, J=8.68, 1.52 Hz), 7.84 (1H, d, J=1.07 Hz), 7.92 (1H, d, J=8.68 Hz), 13.62 (1H, br. s.); LC-MS: m/z=+269.75 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove the volatiles
  3. additiondiluted with EtOAc (30 mL)
  4. washwashed with water
  5. extractionThe aqueous layer was extracted with more EtOAc (20 mL)
  6. washThe combined organics were washed with water (30 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29fa6549e481445b8c5ac5b02e1e19a8
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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