Butyl bromide → HCID 46221940, compound

HRID 1641029Notes

Reaction equation

HRID 1641029 reaction equation
Cl.[CH:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14](=[O:24])[C:15]([NH:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[O:16])=[CH:6]1)([CH3:4])[CH3:3].C([O-])([O-])=O.[K+].[K+].[CH2:31](Br)[CH2:32][CH2:33][CH3:34]>C(#N)C>[CH2:31]([N:21]1[CH2:20][CH2:19][CH:18]([NH:17][C:15](=[O:16])[C:14]([C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:5]([CH:2]([CH3:4])[CH3:3])[CH:6]=2)=[O:24])[CH2:23][CH2:22]1)[CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 66739286HCID 66739286, compound

Product 1

HCID 46221940HCID 46221940, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

The title compound was prepared according to general procedure E described in Scheme 2. 2-(1-Isopropyl-1H-indol-3-yl)-2-oxo-N-(piperidin-4-yl)acetamide hydrochloride (200 mg, 0.64 mmol) was treated with acetonitrile (3 mL), K2CO3 (265 mg, 1.91 mmol), and n-butyl bromide (175 mg, 1.28 mmol). The reaction mixture was stirred at 65° C. for 72 h and was then concentrated under reduced pressure. The crude material was purified on silica gel (Biotage, 2-10% MeOH/DCM, 30 min.) to provide the title compound as a pink solid (68 mg, 29% yield): 1H NMR (400 MHz, CDCl3): δ 9.11 (s, 1H), 8.43 (t, 1H), 7.56 (d, 1H), 7.43 (q, 1H), 7.35 (t, 2H), 4.71 (m, 1H), 3.90 (m, 1H), 3.03 (d, 2H), 2.48 (d, 2H), 2.31 (t, 2H), 2.05 (d, 2H), 1.80 (m, 2H), 1.61 (d+m, 8H), 1.34 (m, 2H), 0.94 (t, 3H);

Workup

  1. customThe title compound was prepared
  2. concentrationwas then concentrated under reduced pressure
  3. customThe crude material was purified on silica gel (Biotage, 2-10% MeOH/DCM, 30 min.)

Sources & evidence

ORD record
ord-49556e2b019d4596b7f9427bda3feda8
Source dataset
uspto-grants-2012_02
Patent number
US08114894B2

Reaction notes

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