Ethylene Glycol → HCID 56592118, compound

HRID 1629917Notes

Reaction equation

HRID 1629917 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]2[CH:27]=[CH:26][C:25]([N+]([O-])=O)=[C:24]3[C:19]=2[CH:20]=[CH:21][N:22]=[CH:23]3)[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:37]([OH:40])[CH2:38][OH:39]>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]2[CH:27]=[CH:26][C:25]([O:39][CH2:38][CH2:37][OH:40])=[C:24]3[C:19]=2[CH:20]=[CH:21][N:22]=[CH:23]3)[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 10796Cesium carbonateHCID 56591859HCID 56591859, compound

Product 1

HCID 56592118HCID 56592118, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A slurry of 198 mg (0.50 mmol) 2-(2-fluoro-phenyl)-4-(8-nitro-isoquinolin-5-yl)-[1,8]naphthyridine (synthesis see example 6) in 1 ml ethane-1,2-diol was treated with 326 mg (1.00 mmol) cesium carbonate. The resulting slurry was stirred at 80° C. for two days. The reaction mixture was cooled to room temperature and diluted with water. The resulting precipitate was filtered off, washed with water and chromatographed on a silica gel column with dichloromethane/methanol as eluent yielding 2-{5-[2-(2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-isoquinolin-8-yloxy}-ethanol as colourless crystals; HPLC/MS: 1.53 min, [M+H] 412.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with water
  4. customchromatographed on a silica gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-160152d4f50446acbff13595fa1b498f
Source dataset
uspto-grants-2014_07
Patent number
US08791113B2

Reaction notes

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