Dimethylformamide → HCID 178505428, compound

HRID 2107399Notes

Reaction equation

HRID 2107399 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)(O)[O-].[Na+].CN(C)C=O>O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][N:14]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7666Phenethyl bromideHCID 516892Sodium BicarbonateHCID 178505426HCID 178505426, compound

Product 1

HCID 178505428HCID 178505428, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 g of 6-fluoro-3-(4-piperidinyl)-1H-indazole, 4.6 g of (2-bromoethyl)benzene, 4.2 g of sodium bicarbonate and 50 ml of dimethylformamide was stirred at 60° for 3 hr and at ambient temperature for 14 hr. The reaction was poured into water and the aqueous mixture extracted with ethyl acetate. The ethyl acetate was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed in vacuo The residue was recrystallized twice from 2-propanol (one charcoal treatment) to yield 2.6 g (35%) of product, mp 163°-165° C.

Workup

  1. extractionthe aqueous mixture extracted with ethyl acetate
  2. washThe ethyl acetate was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo The residue
  5. customwas recrystallized twice from 2-propanol (one charcoal treatment)

Sources & evidence

ORD record
ord-7339cd5e00fa4c078289391e28a56b17
Source dataset
uspto-grants-1990_06
Patent number
US04933460

Reaction notes

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