Sodium borohydride → [1-(6-Tert-butyl-2-chloropyridin-3-yl)ethyl]amine
Reaction equation
[C:1]([C:5]1[N:10]=[CH:9][C:8]([CH:11]([NH2:13])[CH3:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(C#N)=C([Cl:26])N=1)(C)(C)C.C[Mg+].[Br-].[BH4-].[Na+]>>[C:1]([C:5]1[N:10]=[C:9]([Cl:26])[C:8]([CH:11]([NH2:13])[CH3:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]Participants
5
Procedure
The title compound was synthesized according to the procedure described for the synthesis of [1-(6-tert-butylpyridin-3-yl)ethyl]amine starting from 6-tert-butyl-2-chloronicotinonitrile (intermediate 22) (2.0 g, 10.3 mmol), MeMgBr (18 ml, 25.7 mmol) and NaBH4 (970 mg, 25.7 mmol). The resulting material was used crude in the following coupling step. (Yield: 1.76 g, 79%) 1H NMR (400 MHz, CDCl3) δ ppm 1.34 (s, 9 H) 1.39 (d, J=6.64 Hz, 3 H) 4.47 (q, J=6.64 Hz, 1 H) 7.26 (d, J=8.01 Hz, 1 H) 7.78 (d, J=8.01 Hz, 1H).
Sources & evidence
- ORD record
- ord-399004a20c5e4f0897b62d08ec090617
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168668B2
Reaction notes
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