4-Cyanobenzaldehyde → HCID 178434622, compound

HRID 558276Notes

Reaction equation

HRID 558276 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Br.[Cl:16][C:17]1[CH:18]=[C:19]([CH:29]=[C:30]([Cl:32])[CH:31]=1)[O:20][C:21]1[C:22]([CH3:28])=[N:23][NH:24][C:25]=1[CH2:26][NH2:27].[C:33]([C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1)#[N:34]>C(O)(=O)C.ClCCl>[Cl:16][C:17]1[CH:18]=[C:19]([CH:29]=[C:30]([Cl:32])[CH:31]=1)[O:20][C:21]1[C:22]([CH3:28])=[N:23][NH:24][C:25]=1[CH2:26][NH:27][CH2:39][C:38]1[CH:41]=[CH:42][C:35]([C:33]#[N:34])=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178419528HCID 178419528, compound

Product 1

HCID 178434622HCID 178434622, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (216 mg, 1.09 mmol) was added in one portion to a stirred solution of the pyrazole of Example 109 (300 mg, 0.850 mmol), 4-cyanobenzaldehyde (111 mg, 0.850 mmol) and acetic acid (3 drops) in dichloromethane (25 ml) at room temperature tinder nitrogen. The reaction was stirred for 14 hours and then washed with 1M aqueous sodium carbonate solution (2×10 ml) and brine (10 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:4:1, by volume) to provide the title compound (10 mg) as a colourless oil.

Workup

  1. washwashed with 1M aqueous sodium carbonate solution (2×10 ml) and brine (10 ml)
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:4:1, by volume)

Sources & evidence

ORD record
ord-5aa8322a259246a781c5915ac0bbc918
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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