Sodium Hydroxide → HCID 117940033, compound

HRID 62284Notes

Reaction equation

HRID 62284 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.CO.O.[F:22][C:23]([F:39])([F:38])[C:24]([C:30]1[CH:31]=[N:32][CH:33]=[C:34]([CH:37]=1)[CH:35]=O)([OH:29])[C:25]([F:28])([F:27])[F:26].[OH-].[Na+]>C(Cl)(Cl)Cl>[F:28][C:25]([F:26])([F:27])[C:24]([C:30]1[CH:37]=[C:34](/[CH:35]=[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:33]=[N:32][CH:31]=1)([OH:29])[C:23]([F:39])([F:38])[F:22]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 177581373-Pyridinecarboxaldehyde, 5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-HCID 22242641Methanol--water (1/1)HCID 1179401286-Methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 117940033HCID 117940033, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 13 (0.1 g, 0.40 mmol)), MeOH/H2O (1:1), was added 5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)nicotinaldehyde 259 (0.132 g, 0.485 mmol) and NaOH (0.032 g, 0.80 mmol). The reaction was 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 263, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 30% ethyl acetate in hexane to afford yellow coloured solid (E)-2-((5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-3-yl)methylene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 263.

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 263, which
  5. customwas purified through flash chromatography
  6. washThe compound was eluted at 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-19b8e5b3de1d45c78f0b4c8371ecb9a4
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

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