Triethylamine → 6-fluoro-1-(phenylsulfonyl)-3-(1-(pyridazin-3-yl)-1H-pyrazol-4-yl)-1H-indole

HRID 2274840Notes

Reaction equation

HRID 2274840 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[CH:17][C:18]([F:22])=[CH:19][CH:20]=4)[N:15]([S:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:25])=[O:24])[CH:14]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CCN(CC)CC>[Pd]>[F:22][C:18]1[CH:17]=[C:16]2[C:21]([C:13]([C:11]3[CH:10]=[N:9][N:8]([C:5]4[N:6]=[N:7][CH:2]=[CH:3][CH:4]=4)[CH:12]=3)=[CH:14][N:15]2[S:23]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)(=[O:24])=[O:25])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 1180606043-(1-(6-chloropyridazin-3-yl)-1H-pyrazol-4-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole2×

Product 1

HCID 1180605036-fluoro-1-(phenylsulfonyl)-3-(1-(pyridazin-3-yl)-1H-pyrazol-4-yl)-1H-indoleYield 60%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 3-(1-(6-chloropyridazin-3-yl)-1H-pyrazol-4-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole (Intermediate 44; 180 mg; 0.40 mmol), Pd/C(10 mg) and Et3N (40 mg; 0.40 mmol) was stirred for 0.5 hour at r.t. under a hydrogen balloon. The reaction mixture was filtered, concentrated, and purified by a silica gel chromatography (petroleum ether/EtOAc=5/1 to 3/1) to afford 100 mg (60%) of the title compound as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified by a silica gel chromatography (petroleum ether/EtOAc=5/1 to 3/1)

Sources & evidence

ORD record
ord-8599a4c881de48dd9f0b679b3efbf341
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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