Acetic Acid → HCID 178483330, compound

HRID 1398483Notes

Reaction equation

HRID 1398483 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C(O)(=O)C.[CH3:17][NH:18][CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][N:18]([CH3:19])[CH3:17])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178520021HCID 178520021, compound

Product 1

HCID 178483330HCID 178483330, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-bromo-1H-indazole-3-carbaldehyde (300 mg, 1.33 mmol) in THF (1 mL) was added acetic acid (0.11 mL, 2 mmol), 2M dimethylamine in THF (1.33 mL, 2.66 mmol) and sodium triacetoxyborohydride (283 mg, 1.33 mmol). The reaction was stirred at RT for 2 hr then allowed to stand at RT for 18 hr. The mixture was concentrated in vacuo, then diluted with EtOAc (50 mL) and washed with 1M aqueous NaHCO3 (10 mL). The organic layer was washed with brine (5 mL), followed by water (5 mL). The organic layer was then dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a beige solid: 1H NMR (500 MHz, MeOD) δ 2.31 (6H, s), 3.85 (2H, s), 7.27 (1H, dd, J=8.67, 1.58 Hz), 7.68-7.72 (1H, m), 7.77 (1H, d, J=8.67 Hz). LC-MS: m/z=+253.9/255.9 (M+H)+.

Workup

  1. waitto stand at RT for 18 hr
  2. concentrationThe mixture was concentrated in vacuo
  3. additiondiluted with EtOAc (50 mL)
  4. washwashed with 1M aqueous NaHCO3 (10 mL)
  5. washThe organic layer was washed with brine (5 mL)
  6. dry with materialThe organic layer was then dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d69955e7d39543179e1c82ee1916921e
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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