Hydrochloric Acid → 2-(5-(2-Oxo-4-(4-(trifluoromethyl)phenyl)pyridin-1(2H)-yl)-1H-indazol-1-yl)acetaldehyde

HRID 2390435Notes

Reaction equation

HRID 2390435 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:16][C:15]3=[O:30])=[CH:11][CH:12]=2)[CH:7]=[N:6]1.Cl.O>C1COCC1>[O:30]=[C:15]1[CH:16]=[C:17]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=2)[CH:18]=[CH:19][N:14]1[C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][CH:3]=[O:2])[N:6]=[CH:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 576255431-(1-(2,2-Dimethoxyethyl)-1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one

Product 1

HCID 576254982-(5-(2-Oxo-4-(4-(trifluoromethyl)phenyl)pyridin-1(2H)-yl)-1H-indazol-1-yl)acetaldehydeYield 233%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(1-(2,2-dimethoxyethyl)-1H-indazol-5-yl)-4-(4-(trifluoromethyl)-phenyl)pyridin-2(1H)-one (480 mg, 1.08 mmol) in THF (10 mL) was treated with aqueous HCl (9 mL, 2.0 M). The solution was heated to reflux for 1 h, allowed to cool and then treated with H2O (100 mL). The resulting solids were isolated by filtration, washed with H2O and dried under high vacuum for 16 h to give the title compound (1.00 g, 64%) as a light brown solid: ESI MS m/z 398 [M+H]+.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 h
  3. temperatureto cool
  4. customThe resulting solids were isolated by filtration
  5. washwashed with H2O
  6. customdried under high vacuum for 16 h

Sources & evidence

ORD record
ord-967379ad9da544f0b06fc18ef18eeeec
Source dataset
uspto-grants-2012_09
Patent number
US08273770B2

Reaction notes

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