Water → HCID 86601206, compound

HRID 2251970Notes

Reaction equation

HRID 2251970 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[N:7][N:8]([CH2:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)[C:9]=1[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=O.[BH4-].[Na+].O>CO>[F:26][C:23]([F:24])([F:25])[C:21]1[CH:22]=[C:17]([CH:18]=[C:19]([C:27]([F:28])([F:30])[F:29])[CH:20]=1)[CH2:16][N:8]1[C:9]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[C:5]([CH2:3][OH:2])[N:6]=[N:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86601207HCID 86601207, compound

Product 1

HCID 86601206HCID 86601206, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester in MeOH. Add NaBH4 (2.64 g, 3 eq) and warm to reflux overnight (70° C.). Cool to RT and slowly pour into a separatory funnel containing an equal volume of water. Extract with CH2Cl2. Concentrate and recrystallize from EtOAc/Hexanes to give the 7.0 g (75%) of the title compound. MS (IS) 403.2 (M+1); 1H NMR: (400 MHz, CD3OD) δ: 8.65 (dd, J=5.2, 1.6 Hz, 1H) 8.53-8.52 (m, 1H), 7.89 (s, 1H), 7.86-7.83 (m, 1H), 7.60 (s, 2H), 7.56-7.53 (m, 1H), 5.83 (s, 2H), 4.59 (s, 2H).

Workup

  1. temperatureCool to RT
  2. additionslowly pour into a separatory funnel
  3. extractionExtract with CH2Cl2
  4. concentrationConcentrate
  5. customrecrystallize from EtOAc/Hexanes

Sources & evidence

ORD record
ord-e6bbb975aea8447a8bca6203cd3abb7b
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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