Dietylaminopropin → HCID 25222175, compound

HRID 1967206Notes

Reaction equation

HRID 1967206 reaction equation
[C:1]1([CH3:27])[CH:6]=[CH:5][C:4]([N:7]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[C:9](OS(C3C=CC(C)=CC=3)(=O)=O)=[N:8]2)=[CH:3][CH:2]=1.[CH2:28]([N:30]([CH2:34][CH3:35])[CH2:31][C:32]#[CH:33])[CH3:29]>CCCCCCC.CCOC(C)=O>[CH2:28]([N:30]([CH2:34][CH3:35])[CH2:31][C:32]#[C:33][C:9]1[C:10]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:27])=[CH:6][CH:5]=2)[N:8]=1)[CH3:29]

Participants

4

Reactant 2

HCID 20010DietylaminopropinHCID 86646620HCID 86646620, compound

Product 1

HCID 25222175HCID 25222175, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 1-p-tolyl-1H-pyrazolo[3,4-b]pyridin-3-yl ester and diethyl-prop-2-ynyl-amine following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/EtOAc 4:6; yield (64 mg, 40%); 1H NMR δ (CDCl3): 8.64 (m, 1H), 8.19 (m, 1H), 8.11 (d, J=8.52 Hz, 2H), 7.33 (d, J=8.49 Hz, 2H), 7.21-7.28 (m, 1H), 3.86 (s, 2H), 2.73 (q, J=7.17 Hz, 4H), 2.40 (s, 3H), 1.20 (t, J=7.16 Hz, 6H); LCMS m/z: 318.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (64 mg, 40%)

Sources & evidence

ORD record
ord-c3cd923f88d447f5b7e412b5d3a86a1f
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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