Sodium Iodide → HCID 178479659, compound

HRID 1792630Notes

Reaction equation

HRID 1792630 reaction equation
C[O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26]5[C:27]([C:50]([F:53])([F:52])[F:51])=[N:28][N:29](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[CH:30]=5)[CH:24]=4)[N:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.COC1C(CN2CCN(C3C4C(=CC=C(Br)C=4)N=CC=3)CC2)=CC=CN=1.FC(F)(F)C1C(B(O)O)=CN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)N=1.[I-].[Na+].C[Si]([Cl:117])(C)C.S([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O>[ClH:117].[F:53][C:50]([F:51])([F:52])[C:27]1[C:26]([C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[C:16]3[N:13]2[CH2:14][CH2:15][N:10]([CH2:9][C:8]3[C:3](=[O:2])[NH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11][CH2:12]2)=[CH:30][NH:29][N:28]=1

Participants

9

Reactant 6

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 24437Sodium SulfiteHCID 22031142HCID 22031142, compoundHCID 22032227[3-(Trifluoromethyl)-1-trityl-1H-pyrazol-4-YL]boronic acidHCID 68812526HCID 68812526, compound

Product 1

HCID 178479659HCID 178479659, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

117 mg 4-{4-[(2-methoxy-3-pyridyl)methyl]piperazin-1-yl}-6-(3-(trifluoromethyl)-1-trityl-1H-4-pyrazolyl) quinoline prepared by the same method as in Example 168 from 100 mg 3-{[4-(6-bromo-4-quinolyl)piperazin-1-yl]methyl}-2-pyridyl methyl ether (compound in Production Example 460) and 163 mg 3-trifluoromethyl-1-trityl-1H-4-pyrazolylboronic acid (compound in Production Example 31) was dissolved in acetonitrile, and 100 mg sodium iodide, 330 μl trimethyl silyl chloride and 1.5 μl water were added thereto and stirred at 65° C. for 5 hours. After the reaction was finished, the reaction solution was poured into a 1:1 mixture of 5% aqueous sodium sulfite solution and an aqueous saturated sodium chloride solution and then extracted with ethyl acetate. The solvent was removed, and the resulting residue was purified by silica gel column chromatography, and the resulting solid was dissolved in methanol and converted into the corresponding hydrochloride by 4 N hydrogen chloride solution in ethyl acetate. The product was recrystallized from methanol/diethyl ether, to give 20 mg of the title compound.

Workup

  1. extractionan aqueous saturated sodium chloride solution and then extracted with ethyl acetate
  2. customThe solvent was removed
  3. customthe resulting residue was purified by silica gel column chromatography
  4. dissolutionthe resulting solid was dissolved in methanol
  5. customThe product was recrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-bcb3acbbd13c4841af74902aed5f3240
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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