Aluminium lithium hydride → 4-aminomethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 1352011Notes

Reaction equation

HRID 1352011 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][N:15]2[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)=[N+]=[N-]>O1CCCC1>[NH2:7][CH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][N:15]2[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22661453HCID 22661453, compound

Product 1

HCID 226611964-aminomethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of lithium aluminum hydride in tetrahydrofuran (1.0 M; 0.51 mL, 0.51 mmol) was added dropwise over 12 min to a cooled (0° C.) solution of 4-azidomethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (130 mg, 0.505 mmol) in dry tetrahydrofuran (1.5 mL). The solution was stirred at ˜0° C. for 1 h and then quenched with 1 M sodium hydroxide (75 μL) over approx. 1 min. The cooling bath was removed and the mixture was stirred for 1 h. The mixture was diluted with ethyl acetate (3 mL), dried (Na2SO4), filtered through Celite (which was washed with ethyl acetate), and concentrated to give 4-aminomethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (106 mg, 91%) as a yellow solid.

Workup

  1. customquenched with 1 M sodium hydroxide (75 μL) over approx. 1 min
  2. customThe cooling bath was removed
  3. stirringthe mixture was stirred for 1 h
  4. additionThe mixture was diluted with ethyl acetate (3 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered through Celite (which was washed with ethyl acetate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c8b3a25945724340acd9aa87e5e3a541
Source dataset
uspto-grants-2007_05
Patent number
US07217728B2

Reaction notes

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