Ethyl bromoacetate → HCID 71227120, compound

HRID 713438Notes

Reaction equation

HRID 713438 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:8])[CH2:3][CH2:2]1.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(N(CC)CC)C>C(#N)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][N:1]1[CH2:6][CH2:5][CH:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:8])[CH2:3][CH2:2]1)[CH3:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 9943756HCID 9943756, compound

Product 1

HCID 71227120HCID 71227120, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of compound piperidin-4-yl-pyridin-2-yl-methanone (170 mg, 0.894 mmol) in 10 mL acetonitrile was added ethyl bromoacetate (0.13 mL, 1.12 mmol) and triethylamine (362 mg, 3.57 mmol). The reaction was heated at 80° C. for 16 hour. The combined organic layers were concentrated under vacuum to afford an orange oily solid. The residue was chromatographed on silica gel (gradient: methanol/dichloromethane; 0:1 to 1:9 over 20 minutes) to afford the title compound as a white solid (198 mg). 1H NMR (400 MHz, CDC3) δ 8.68 (d, J=4.0 Hz, 1H), 8.06 (d, J=7.6 Hz, 1H), 7.89 (t, J=9.0 Hz, 1H), 7.52 (t, J=7.6 Hz, 1H), 4.33-4.27 (m, 2H), 3.92 (s, 2H), 3.70-3.72 (m, 2H), 3.59-3.53 (m, 2H), 2.34-2.28 (m, 4H), 1.34 (t, J=7.1 Hz, 3H). MS m/z ES+=276.8 (M+H), retention time 0.80.

Workup

  1. concentrationThe combined organic layers were concentrated under vacuum
  2. customto afford an orange oily solid
  3. customThe residue was chromatographed on silica gel (gradient: methanol/dichloromethane; 0:1 to 1:9 over 20 minutes)

Sources & evidence

ORD record
ord-bc1802e9283b420b83cf69fe3c3a6f55
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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