1,2-Dimethoxyethane → HCID 22709560, compound

HRID 1708382Notes

Reaction equation

HRID 1708382 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.CO[CH2:12][CH2:13][O:14][CH3:15].[C:16](=[O:19])([O-])[O-:17].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:15][O:14][C:13]1[CH:12]=[C:2]([CH:3]=[CH:4][C:5]=1[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[C:16]([OH:17])=[O:19]

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 22709560HCID 22709560, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

Intermediate 38 (1.06 g), 4-pyridinylboronic acid (486 mg), DME (25 ml), 2N sodium carbonate (10 ml) and tetrakis(triphenylphosphine) palladium (0) (70 mg), were heated to reflux for 18 h under nitrogen. After allowing to cool to room temperature, water (50 ml) was added and the mixture was washed with ethyl acetate (2×50 ml). The aqueous phase was neutralised with 2N hydrochloric acid, and then concentrated in vacuo onto silica (Merck 9385). Purification by FCC eluting with ethyl acetate:hexane:acetic acid (750:240:10) gave a pale orange solid which was triturated in ether and dried under high vacuum to give the title compound as a pale orange solid (370 mg) m.p. 239°-241° C.

Workup

  1. temperatureto reflux for 18 h under nitrogen
  2. washthe mixture was washed with ethyl acetate (2×50 ml)
  3. concentrationconcentrated in vacuo onto silica (Merck 9385)
  4. customPurification by FCC
  5. washeluting with ethyl acetate:hexane:acetic acid (750:240:10)
  6. customgave a pale orange solid which
  7. customwas triturated in ether
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-83cafae483694fed86891eec41a8ab68
Source dataset
uspto-grants-1994_10
Patent number
US05358948

Reaction notes

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