Ethyl Acetate → 1h-Indazole-6-methanamine,1-(tetrahydro-2h-pyran-2-yl)-

HRID 1263441Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]([CH2:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[N:16][N:17]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:13][CH:12]=1)=[N+]=[N-].[OH-].[Na+].C(OCC)(=O)C>C1COCC1>[NH2:7][CH2:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[N:16][N:17]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of LiAlH4 (9 mL, 9 mmol, 1.0 M) in THF was added dropwise to a yellow solution of 6-(azidomethyl)-1-(2-tetrahydropyranyl)indazole (2.4 g, 9 mmol) (101) in THF (30 mL) at 0° C. The addition time was 10 minutes, and gas came out. After stirring at 0° C. for 1 hour, NaOH (1.0 m, 1.5 mL) was added. The reaction mixture was allowed to warm to room temperature. Ethyl acetate (100 mL) was added, and the suspension was filtered through (Celite). The filter cake was washed with an addition portion of ethyl acetate (40 mL). Combined organic layers were evaporated under vacuum to five essentially pure amine (2.1 g, 97%). MS (electrospray) 232.5 (M+1); 1H NMR (CDCl3) δ1.67 (m, 3H), 2.01 (m, 2H), 2.48 (m, 1H), 3.85 (m, 1H), 3.94 (m, 1H), 5.75 (d, 1H, J=9.4 Hz), 7.14 (d, 1H, J=8.4 Hz), 7.62 (s, 1H), 7.62 (d, 1H, J=8.4 Hz), 7.93 (s, 1H).

Workup

temperatureto warm to room temperature
filtrationthe suspension was filtered through (Celite)
washThe filter cake was washed with an addition portion of ethyl acetate (40 mL)
customCombined organic layers were evaporated under vacuum to five essentially pure amine (2.1 g, 97%)

Sources & evidence

ORD record: ord-82ec485aaffa4b7db2bf75d48e872290
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541467B1

Reaction notes

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