Triethylamine → HCID 131728143, compound

HRID 2241035Notes

Reaction equation

HRID 2241035 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=[CH:4][CH:3]=1.CCN(CC)CC.[C:32]([O:36][CH2:37][CH3:38])(=[O:35])[CH:33]=[CH2:34]>CN(C=O)C>[C:19]1([C:8](=[C:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)[C:5]2[CH:6]=[CH:7][C:2](/[CH:34]=[CH:33]/[C:32]([O:36][CH2:37][CH3:38])=[O:35])=[CH:3][CH:4]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 68501670HCID 68501670, compound

Product 1

HCID 131728143HCID 131728143, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A yellow solution of 16, Et3N, ethyl acrylate and dichlorobis(triphenylphosphine) palladium(II) in DMF (25 mL, anhydrous, Aldrich) was stirred overnight under N2 at 110° C. After 16 h the reaction was allowed to cool to RT, filtered, and the filtrate diluted with ether (100 mL) and water (100 mL). The ether layer was rinsed with water (2×75 mL) and brine (1×74 mL) then dried (MgSO4) and concentrated to 5.75 g of a yellow solid. The crude product was purified first by column chromatography on 250 g silica gel with 2% EtOAc/hexanes to yield 6.22 g of an impure white solid. Crystallization from hexanes (˜100 mL) afforded 2.39 g (55%) of the title compound 17 as a crystalline white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.63 (d, J=8.0 Hz, 2H), 7.59 (d, J=16.1 Hz, 1H), 7.15-7.30 (m, 7H), 6.56 (d, J=16.1 Hz, 1H), 4.15 (q, J=7.1 Hz, 2H), 1.91 (s, 2H), 1.88 (s, 2H), 1.21-1.25 (m, 5H), 0.88 (s, 6H), 0.87 (s, 6H).

Workup

  1. filtrationfiltered
  2. additionthe filtrate diluted with ether (100 mL) and water (100 mL)
  3. washThe ether layer was rinsed with water (2×75 mL) and brine (1×74 mL)
  4. dry with materialthen dried (MgSO4)
  5. concentrationconcentrated to 5.75 g of a yellow solid
  6. customThe crude product was purified first by column chromatography on 250 g silica gel with 2% EtOAc/hexanes

Sources & evidence

ORD record
ord-a28c6601309b4c2ab77d40afa4dc780b
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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