1-Bromo-3-methylbutane → HCID 58966937, compound

HRID 1948236Notes

Reaction equation

HRID 1948236 reaction equation
[O:1]=[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][NH:3]1.Br[CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19]>C(#N)C.CCCCC.CCOCC>[CH2:16]([N:3]1[CH:4]=[CH:5][C:6]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[C:7]([C:8]#[N:9])[C:2]1=[O:1])[CH2:17][CH:18]([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 78911-Bromo-3-methylbutaneHCID 2764405HCID 2764405, compound

Product 1

HCID 58966937HCID 58966937, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21877078Diethylether pentaneSolvent

Procedure

According to Scheme 21: The title compound was prepared according to Example 1 Step 2 from 1,2-dihydro-2-oxo-4-(thiophen-2-yl)pyridine-3-carbonitrile (1 eq, 0.50 mmol, 0.10 g) and 1-bromo-3-methylbutane (1.5 eq, 0.70 mmol, 0.10 g). Reaction conditions: 17 hours at 60° C. in acetonitrile (10 mL). The crude product was purified by chromatography over silicagel (AIT Flashsmart prepacked column SiO2, cyclohexane/AcOEt 80/20) and recrystallized in pentane/Et2O yielding the title compound (88 mg, 0.30 mmol, 65%) as a yellow solid. M.p.: 123° C.; LC (XTerra RP18, 3.5 μm, 3.0×50 mm Column): RT=4.29 min; MS m/z (CI) [MH]+=273; 1H NMR (300 MHz, DMSO-d6) δ 0.92 (d, J=5.6 Hz, 6H), 1.48-1.63 (m, 3H), 3.90-4.02 (m, 2H), 6.72 (d, J=7.2 Hz, 1H), 7.32 (d, J=8.4 Hz, 1H), 7.96-8.04 (m, 2H), 8.08 (d, J=7.2 Hz, 1H).

Workup

  1. customThe title compound was prepared
  2. customReaction conditions
  3. custom17 hours
  4. customat 60° C.
  5. customThe crude product was purified by chromatography over silicagel (AIT Flashsmart prepacked column SiO2, cyclohexane/AcOEt 80/20)

Sources & evidence

ORD record
ord-3871139bf04b43359e4e4483fc74ed76
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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