Water → HCID 10292063, compound

HRID 1374705Notes

Reaction equation

HRID 1374705 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:11]3[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].I[CH2:31][CH2:32][CH2:33][CH3:34].O>CN(C)C=O.C1COCC1>[CH2:31]([O:16][C:13]1[CH:14]=[CH:15][N:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:11]2[CH:12]=1)[CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 962WaterHCID 10962Butyl iodide2×HCID 23665647Potassium tert-butoxide2×HCID 178516348HCID 178516348, compound

Product 1

HCID 10292063HCID 10292063, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridin-5-ol (Example 24. 0.5 g, 1.63 mmol) was dissolved in dimethylformamide (10 mL) and potassium tert butoxide (2.5 mL of a 1 M solution in THF, 2.5 mmol) was added dropwise to the stirred solution. After 10 minutes iodobutane (2 mmol) was added and the reaction stirred at room temperature. Second additions of iodobutane (0.88 mmol) and 1M potassium tertbutoxide (2.5 mL, 1 mmol) were made after 4 h and reaction stirred further until complete by TLC. Water (100 mL) was added and the resulting aqueous solution was extracted with with dichloromethane (4×100 mL), the combined organic solution was dried (MgSO4), filtered and concentrated to give the crude product. This was purified either by silica gel chromatography to give the title compound (58%). 1H NMR (d6-DMSO) δ 0.93 (t, J=7.3 Hz, 3H), 1.43 (quintet, J=7.3 Hz, 2H), 1.74 (quintet, J=7.3 Hz, 2H), 4.13 (t, J=6.9 Hz, 2H), 6.84 (dd, J=2.4, 7.5 Hz, 1H), 7.21 (d, J=2.4 Hz, 1H), 7.28 (t, J=8.8 Hz, 2H), 7.53 (dd, J=0.5, 8.8 Hz, 2H), 7.73 (d, J=6.4 Hz, 2H), 8.65 (d, J=6.4 Hz, 2H), 8.74 (d, J 7.5 Hz, 1H); APESI-MS m/z 362 (M+1)+.

Workup

  1. customreaction
  2. stirringstirred further until complete by TLC
  3. extractionthe resulting aqueous solution was extracted with with dichloromethane (4×100 mL)
  4. dry with materialthe combined organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customThis was purified either by silica gel chromatography

Sources & evidence

ORD record
ord-16f5529b87874f48ab4e248f80892f4d
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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