Pyridine → HCID 68851274, compound

HRID 1292985Notes

Reaction equation

HRID 1292985 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][C:22]=2[O:23][CH3:24])[NH:19][N:18]=[C:17]3[S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34]1(B(O)O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.N1C=CC=CC=1.C(Cl)[Cl:50]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[ClH:50].[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][C:22]=2[O:23][CH3:24])[N:19]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:18]=[C:17]3[S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:26])=[O:27])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 178486924HCID 178486924, compound

Product 1

HCID 68851274HCID 68851274, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

A mixture of 5-(4-benzylpiperazin-1-yl)-6-methoxy-3-(phenylsulfonyl)-1H-indazole (448 mg, 0.97 mmol), phenylboronic acid (242 mg, 1.94 mmol), copper(II) acetate (271 mg, 1.50 mmol), pyridine (160 mg, 2.00 mmol) and 4 Å molecular sieves (1.0 g) in methylene chloride is stirred at room temperature for 48 h and filtered. The filtercake is washed with THF. The filtrates are combined and concentrated in vacuo. The resultant residue is chromatographed (silica gel, 60:40 and 80:20 ethyl acetate:hexanes as eluents) to afford the free amine of the title product as a white solid, 130 mg (25% yield). The free amine is dissolved in ethanol, treated with 4.0 M HCl in dioxane, and concentrated in vacuo to a solid residue. This solid is triturated with ethyl acetate to afford the title product as a white solid, mp: 210–212° C., identified by NMR and mass spectral analyses.

Workup

  1. filtrationfiltered
  2. washThe filtercake is washed with THF
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue is chromatographed (silica gel, 60:40 and 80:20 ethyl acetate:hexanes as eluents)

Sources & evidence

ORD record
ord-5a421678a8cc4cf0b376abeaf047e459
Source dataset
uspto-grants-2007_07
Patent number
US07238696B2

Reaction notes

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