Dimethylformamide → HCID 178456220, compound

HRID 986125Notes

Reaction equation

HRID 986125 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][CH3:20].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][CH3:20])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78401-BromopropaneHCID 516892Sodium BicarbonateHCID 178505426HCID 178505426, compound

Product 1

HCID 178456220HCID 178456220, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.0 g of 6-fluoro-3-(4-piperidinyl)-1H-indazole, 1.8 g of 1-bromopropane, 2.5 g of sodium bicarbonate and 30 ml of dimethylformamide was stirred and heated at 60° for 2 hr. After stirring at ambient temperature for 14 hr, the reaction was poured into water and the aqueous suspension was extracted with ethyl acetate. The ethyl acetate was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed in vacuo. Recrystallization of the residue from ethyl acetate yielded 2.3 g (63%) of product. This material was combined with a sample from another experiment and recrystallized from ethyl acetate to yield the analytical sample, mp 175°-177° C.

Workup

  1. temperatureheated at 60° for 2 hr
  2. stirringAfter stirring at ambient temperature for 14 hr
  3. extractionthe aqueous suspension was extracted with ethyl acetate
  4. washThe ethyl acetate was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-18dc103210c54528be3231565f2c0f3b
Source dataset
uspto-grants-1987_12
Patent number
US04710573

Reaction notes

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