Methyl iodide → HCID 69589121, compound

HRID 859141Notes

Reaction equation

HRID 859141 reaction equation
[CH2:1]([C:3]1[C:11]([NH:12][CH2:13][CH2:14][CH2:15][F:16])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].[C:17]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH2:1]([C:3]1[C:11]([N:12]([CH2:13][CH2:14][CH2:15][F:16])[CH3:17])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 45095432HCID 45095432, compound

Product 1

HCID 69589121HCID 69589121, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-ethyl-N-(3-fluoropropyl)pyrazolo[1,5-a]pyridin-3-amine (0.301 g, 1.36 mmol) in DMF (4 mL) was treated with K2CO3 (0.200 g, 1.45 mmol) and methyl iodide (0.06 mL, 0.96 mmol). The reaction was stirred at room temperature for 22 hours then concentrated in vacuo. The residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2 and the combined organics was dried over MgSO4, concentrated in vacuo to give 0.190 g (84%) of a brown oil as the title compound: 1H NMR (400 MHz, DMSO-d6) δ 8.46 (d, J=6.9 Hz, 1H), 7.57 (d, J=8.9 Hz, 1H), 7.08–7.05 (m, 1H), 6.73–6.70 (m, 1H), 4.56 (dt, J=47.5, 5.9 Hz, 2H), 3.09 (t, J=7.0 Hz, 2H), 2.78 (s, 3H), 2.71 (q, J=7.6 Hz, 2H), 1.77–1.64 (m, 2H), 1.24 (t, J=7.6, Hz 3H); 13C NMR (100 MHz, DMSO-d6) δ 152.3, 135.2, 128.7, 122.1, 120.9, 116.4, 110.6, 82.6 (d, J=161.4 Hz), 52.4 (d, J=5.2 Hz), 43.6, 29.0 (d, J=19.3 Hz), 19.0, 13.5; 19F NMR (376 MHz, DMSO-d6) −219.0 (m); HRMS (FAB) calcd for C13H18FN3+H 236.1563. found 236.1573.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between CH2Cl2 and water
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialthe combined organics was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9262b673d15848d194c840b4773326ce
Source dataset
uspto-grants-2006_12
Patent number
US07151109B2

Reaction notes

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