Diethyl Ether → HCID 59599578, compound

HRID 2267022Notes

Reaction equation

HRID 2267022 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[H-].[Na+].Br[C:14]1[N:19]=[C:18]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([OH:31])[C:23]=2[CH2:32][CH2:33][CH3:34])[CH:17]=[CH:16][CH:15]=1.C(OCC)C>CN(C)C=O>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C:18]2[N:19]=[C:14]([S:1][C:2]3[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=3)[C:5]([OH:7])=[O:6])[CH:15]=[CH:16][CH:17]=2)=[C:23]([CH2:32][CH2:33][CH3:34])[C:24]=1[OH:31])(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 95737Benzoic acid, 3-mercapto-HCID 866198461-[4-(6-Bromo-pyridin-2-ylmethoxy)-2-hydroxy-3-propyl-phenyl]-ethanone

Product 1

HCID 59599578HCID 59599578, compoundYield 5.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-mercaptobenzoic acid (361 mg, 2.35 mmol) in dimethylformamide (15 mL) add sodium hydride (23 mg, 9.38 mmol) at 0° C., stir 10 min. Add 1-[4-(6-bromo-pyridin-2-ylmethoxy)-2-hydroxy-3-propyl-phenyl]-ethanone (854 mg, 2.35 mmol), heat to 100° C. for 6 hours. Cool to ambient temperature and add diethyl ether, collect the resulting red precipitate by filtration (290 mg). Purify by the residue by preparative LC (inject 110 mg) to yield the title compound as a white solid (50 mg, 0.12 mmol): 1H NMR (DMSO-d6) δ 0.88 (t, 3H), 1.50 (q, 2H), 2.55 (s, 3H), 2.61 (m, 2H), 5.25 (s, 2H), 6.65 (d, 1H), 6.97 (d, 1H), 7.26 (d, 1H), 7.62 (t, 1H), 7.76 (m, 1H), 7.83 (m, 1H), 8.02 (m, 1H), 8.07 (m, 1H), 12.85 (s, 1H), 13.25 (br s, 1H); MS (m/z): 436 (M−1).

Workup

  1. customcollect the resulting red precipitate
  2. filtrationby filtration (290 mg)
  3. customPurify by the residue by preparative LC (inject 110 mg)

Sources & evidence

ORD record
ord-80ecec9fae20464fbd1a7ce18bb7f17b
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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