Water → Ethyl 2-(5-bromo-7-chlorobenzofuran-2-yl)ethyl(2,2-dimethoxyethyl)carbamate

HRID 2179428Notes

Reaction equation

HRID 2179428 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:20])[C:5]2[O:9][C:8]([CH2:10][CH2:11][NH:12][CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16])=[CH:7][C:6]=2[CH:19]=1.C(N(C(C)C)CC)(C)C.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32].O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([Cl:20])[C:5]2[O:9][C:8]([CH2:10][CH2:11][N:12]([CH2:13][CH:14]([O:15][CH3:16])[O:17][CH3:18])[C:31](=[O:32])[O:33][CH2:34][CH3:35])=[CH:7][C:6]=2[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 68109284N-(2-(5-bromo-7-chlorobenzofuran-2-yl)ethyl)-2,2-dimethoxyethanamine

Product 1

HCID 68109872Ethyl 2-(5-bromo-7-chlorobenzofuran-2-yl)ethyl(2,2-dimethoxyethyl)carbamateYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product obtained from step A (640 mg, 1.76 mmol) in dichloromethane (5 mL) at 0° C. was added diisopropylethylamine (0.61 mL, 3.53 mmol) followed by ethyl chloroformate (0.34 mL, 3.53 mmol). The reaction mixture was allowed to warm to ambient temperature over 2 h before addition of water (10 mL). The mixture was extracted with dichloromethane (2×20 mL) and the combined organic extracts washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification by flash column chromatography (SiO2, 9:1 to 1:1 hexanes/ethyl acetate) afforded ethyl 2-(5-bromo-7-chlorobenzofuran-2-yl)ethyl(2,2-dimethoxyethyl)carbamate (685 mg, 89%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 7.51 (s, 1H), 7.37 (s, 1H), 6.50-6.39 (m, 1H), 4.53-4.38 (m, 1H), 4.21-3.98 (m, 2H), 3.75-3.64 (m, 2H), 3.47-3.35 (m, 6H), 3.34-3.22 (m, 2H), 3.13-2.99 (m, 2H), 1.30-1.11 (m, 3H).

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×20 mL)
  2. washthe combined organic extracts washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customPurification by flash column chromatography (SiO2, 9:1 to 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e4439c7008d54486b7045f9d3c583063
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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