1-Butanol → HCID 57884143, compound

HRID 1818078Notes

Reaction equation

HRID 1818078 reaction equation
F[C:2]1[N:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5].[CH2:19]([OH:23])[CH2:20][CH2:21][CH3:22].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>>[CH2:19]([O:23][C:2]1[N:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 66724543HCID 66724543, compound

Product 1

HCID 57884143HCID 57884143, compoundYield 86.5%

Procedure

2-Fluoro-N-phenethyl-nicotinamide (196 mg, 0.802 mmol), n-butanol (700 μL, 7.65 mmol) and potassium bis(trimethylsilyl)amide (2.5 mL, 0.5 M in toluene) were combined and stirred for 5 minutes at room temperature. The reaction mixture was evaporated to dryness and purified by column chromatography on silica gel using a gradient of 0-20% ethyl acetate in hexanes. The pure fractions were combined and evaporated to dryness to yield a colorless oil (207 mg, 0.694 mmol, 86.5%). ESI-MS m/z calc. 298.2, found 299.2 (M+1)+. Retention time of 3.46 minutes. H NMR (400 MHz, CD3CN) δ, 0.95 (t, J=7.4 Hz, 3H), 1.34-1.44 (m, 2H), 1.63-1.70 (m, 2H), 2.91 (t, J=7.0 Hz, 2H), 3.65-3.73 (m, 2H), 4.41 (t, J=6.7 Hz, 2H), 7.08 (dd, J=7.5, 4.8 Hz, 1H), 7.23-7.37 (m, 5H), 8.01 (s, 1H), 8.25 (dd, J=4.8, 2.0 Hz, 1H), 8.39 (dd, J=7.5, 2.0 Hz, 1H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by column chromatography on silica gel using a gradient of 0-20% ethyl acetate in hexanes
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-52fb72abdafe4a3a90fcf38f76d0b3ac
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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