Potassium Carbonate → (E)-(5-Bromo-6-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}pyridin-3-yl)-2-(4-hydroxyphenyl)-ethylene

HRID 77248Notes

Reaction equation

HRID 77248 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][C:23]([O:26]C(=O)C)=[CH:22][CH:21]=2)[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][F:17].C([O-])([O-])=O.[K+].[K+]>CCO.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4](/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][F:17]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 16221622(E)-(5-Bromo-6-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}pyridin-3-yl)-2-(4-acetoxyphenyl)-ethylene

Product 1

HCID 16221447(E)-(5-Bromo-6-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}pyridin-3-yl)-2-(4-hydroxyphenyl)-ethyleneYield 97%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Acetate 11d (0.145 g, 0.31 mmol) and K2CO3 (0.064 g, 0.465 mmol) were placed in EtOH/THF (5 mL/5 mL) and the reaction mixture was stirred at r.t. 2 h. After standard workup with EtOAc, the crude product was purified by PTLC to give 11e as a white solid (0.128 g, 97%). 1H NMR δ8.07 (d, 1H, J=2.1 Hz), 7.99 (d, 1H, J=2.1 Hz), 7.35 (d, 2H, J=8.6 Hz), 6.96-6.74 (m, 4H), 5.22 (br s, 1H), 4.69 (t, 1H, J=4.2 Hz), 4.54 (t, 2H, J=4.8 Hz), 4.45 (t, 1H, J=4.2 Hz), 3.94-3.68 (m, 8H). 13C NMR δ 158.5, 156.4, 143.6, 138.2, 129.2, 129.0, 127.9, 120.7, 116.0, 107.6, 84.9, 81.6, 71.1, 71.0, 70.8, 70.4, 69.6, 66.8. HRMS calcd for C19H21BrFNO4 (M+), 425.0638; found, 425.0651.

Workup

  1. custom2 h
  2. customAfter standard workup with EtOAc, the crude product was purified by PTLC

Sources & evidence

ORD record
ord-645a08a6ce7847808facc7b27a7faf28
Source dataset
uspto-grants-2014_09
Patent number
US08840866B2

Reaction notes

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