HCID 594324, compound → HCID 69588575, compound

HRID 859149Notes

Reaction equation

HRID 859149 reaction equation
[CH3:1][C:2]1[C:10]([C:11](=O)[CH3:12])=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:14][Mg]Br>CCOCC>[C:11]([C:10]1[C:2]([CH3:1])=[N:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12)([CH3:12])=[CH2:14]

Participants

4

Reactant 2

HCID 594324HCID 594324, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 69588575HCID 69588575, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 0° C. solution of 1-(2-methylpyrazolo[1,5-a]pyridin-3-yl)ethanone (1.05 g, 6.0 mmol) in ether (20 mL) was treated with 3.0 M ether solution of methyl magnesium bromide (4 mL, 12.0 mmol). The reaction was allowed to warm to room temperature and stirred for 7 hours. The reaction was quenched with 2N HCl then extracted with ethyl acetate, washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (50% ethyl acetate/heptane) to give 0.562 g (55%) of brown oil as the title compound: 1H NMR (400 MHz, DMSO-d6) δ 8.53 (d, J=7.0 Hz, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.19–7.15 (m, 1H), 6.82–6.78 (m, 1H), 5.20–5.19 (m, 1H), 5.04–5.03 (m, 1H), 2.42 (s, 3H), 2.16 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ 148.1, 137.5, 136.1, 128.2, 123.7, 117.0, 113.7, 111.2, 110.7, 23.6, 13.6; HRMS (FAB) calcd for C11H12N2+H 173.1079. found 173.1076.

Workup

  1. customThe reaction was quenched with 2N HCl
  2. extractionthen extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-02b7d46f9a2d44fdaab5ddada705c22e
Source dataset
uspto-grants-2006_12
Patent number
US07151109B2

Reaction notes

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