Acetic Acid → HCID 117728065, compound

HRID 60844Notes

Reaction equation

HRID 60844 reaction equation
[CH2:1]=[C:2]([C:4]1[C:5]([C:10]#[N:11])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:3].[C:12]([OH:15])(=[O:14])[CH3:13]>[Pd]>[C:12]([OH:15])(=[O:14])[CH3:13].[CH:2]([C:4]1[C:5]([CH2:10][NH2:11])=[N:6][CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 897412943-(Prop-1-en-2-yl)picolinonitrile

Product 1

HCID 117728065HCID 117728065, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 3-(prop-1-en-2-yl)picolinonitrile in acetic acid was added 10% Pd/C. The Parr shaker bottle was evacuated/H2 purged 3×, and then shaken at 50 psi until starting material was consumed (typically <1 h). The reaction was filtered through diatomaceous earth and concentrated to yield (3-isopropylpyridin-2-yl)methanamine acetic acid salt which was used without further purification. To the crude salt in THF was added aq 1M NaOH, followed by BOC2O (2 eq). The reaction was allowed to stir at rt overnight. After ˜16 h, the reaction mixture was transferred to a seperatory funnel, diluted with EtOAc, and water, and the layers were separated. The organic layer was washed with brine, dried (MgSO4), and concentrated in vacuo to give a crude residue which was purified by chromatography on silica gel (EtOAc/hex) to afford the title compound as a clear oil. 1H NMR (CDCl3, 400 MHz) δ 8.4 (m, 1H), 7.5 (m, 1H), 7.2 (m, 1H), 4.5 (s, 2H), 3.1 (s, 1H), 1.4 (s, 9H), 1.2 (d, J=3.5 Hz, 6H)

Workup

  1. customThe Parr shaker bottle was evacuated/H2
  2. custompurged 3×
  3. customwas consumed (typically <1 h)
  4. filtrationThe reaction was filtered through diatomaceous earth
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f3a667fa8bff4ccdbe57300522a28157
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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