Sodium Carbonate → HCID 14032660, compound

HRID 986175Notes

Reaction equation

HRID 986175 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.Cl.FC1C=C2C(C(C3CCNCC3)=NN2C2C=CC=CC=2)=CC=1.Cl[CH2:47][CH2:48][CH2:49][CH:50]([C:58]1[CH:63]=[CH:62][C:61]([F:64])=[CH:60][CH:59]=1)[C:51]1[CH:56]=[CH:55][C:54]([F:57])=[CH:53][CH:52]=1.C([O-])([O-])=O.[Na+].[Na+]>O.CC(C)CC(=O)C>[F:57][C:54]1[CH:53]=[CH:52][C:51]([CH:50]([C:58]2[CH:59]=[CH:60][C:61]([F:64])=[CH:62][CH:63]=2)[CH2:49][CH2:48][CH2:47][N:20]2[CH2:21][CH2:22][CH:17]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=4)[N:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[N:7]=3)[CH2:18][CH2:19]2)=[CH:56][CH:55]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 14032612HCID 14032612, compoundHCID 14032613HCID 14032613, compound

Product 1

HCID 14032660HCID 14032660, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A stirred mixture, under nitrogen, of 6-fluoro-1-phenyl-3-(4-piperidinyl)-1H-indazole (1.5 g, 0.005 mol), the free base of Example 98, 4-chloro-1,1-bis-(4-fluorophenyl)butane (1.6 g, 0.0056 mol), Na2CO3 (0.6 g), a few crystals of KI and 4-methyl-2-pentanone (70 ml) was refluxed for 16 hours. The reaction was poured into H2O, and the aqueous mixture extracted with ethyl acetate. The ethyl acetate was washed (H2O), dried (MgSO4) and the solvent was concentrated to a liquid. The liquid was dissolved in anhydrous ether and HCl (g) was added to precipitate a gum. The supernatant ether was decanted, H2O was added to the gum, and the mixture was made basic with NH4OH. The basic suspension was extracted with ether, the extract washed (H2O), dried (MgSO4), and the solvent was concentrated to yield 0.64 g (24%) of a solid. This material was combined with 2.9 g of a compound from another run and recrystallized from isopropyl ether to yield 2.1 g of 3-[1-[4,4-bis(4-fluorophenyl)butyl-4-piperidinyl]-6-fluoro-1-phenyl-1H-indazole, mp 113°-115° C.

Workup

  1. extractionthe aqueous mixture extracted with ethyl acetate
  2. washThe ethyl acetate was washed (H2O)
  3. dry with materialdried (MgSO4)
  4. concentrationthe solvent was concentrated to a liquid
  5. dissolutionThe liquid was dissolved in anhydrous ether
  6. additionHCl (g) was added
  7. customto precipitate a gum
  8. customThe supernatant ether was decanted
  9. additionH2O was added to the gum
  10. extractionThe basic suspension was extracted with ether
  11. washthe extract washed (H2O)
  12. dry with materialdried (MgSO4)
  13. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-e4c7712a891b478a9958a2d8a3005603
Source dataset
uspto-grants-1987_12
Patent number
US04710573

Reaction notes

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