Sodium Hydroxide → HCID 117940184, compound

HRID 62285Notes

Reaction equation

HRID 62285 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[F:19][C:20]([F:36])([F:35])[C:21]([C:27]1[N:32]=[C:31]([CH:33]=O)[CH:30]=[CH:29][CH:28]=1)([OH:26])[C:22]([F:25])([F:24])[F:23].[OH-].[Na+]>CO.O.C(Cl)(Cl)Cl>[F:25][C:22]([F:23])([F:24])[C:21]([C:27]1[N:32]=[C:31](/[CH:33]=[C:8]2/[C:9](=[O:12])[C:10]3[C:6]([CH2:7]/2)=[CH:5][C:4]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[C:3]([O:2][CH3:1])[CH:11]=3)[CH:30]=[CH:29][CH:28]=1)([OH:26])[C:20]([F:36])([F:35])[F:19]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 1179401286-Methoxy-5-morpholino-2,3-dihydro-1H-inden-1-oneHCID 117940185HCID 117940185, compound

Product 1

HCID 117940184HCID 117940184, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 13 (0.1 g, 0.40 mmol)) in MeOH/H2O (1:1) was added 6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)picolinaldehyde 262 (0.132 g, 0.485 mmol), NaOH (0.032 g, 0.80 mmol), and the reaction stirred at RT for 6 h. The reaction mass was diluted with chloroform and washed with water (3×25 ml). The organic layer was dried over sodium sulphate and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound 265 was eluted at 30% ethyl acetate in hexane to afford yellow coloured solid (E)-2-((6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-2-yl)methylene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 265.

Workup

  1. washwashed with water (3×25 ml)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. concentrationconcentrated
  4. customto get the crude, which
  5. customwas purified through flash chromatography
  6. washThe compound 265 was eluted at 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8e8c0900447543b09a1507eef8c64a33
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

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