Pyridine → HCID 69371258, compound

HRID 2181519Notes

Reaction equation

HRID 2181519 reaction equation
[CH:1]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=3)=[CH:15][CH:16]=2)[N:11]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:40](Cl)(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C(Cl)Cl>[CH:1]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([NH:18][C:19]3[CH:20]=[C:21]([NH:25][C:40](=[O:47])[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[CH:22]=[CH:23][CH:24]=3)=[CH:15][CH:16]=2)[N:11]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:33])[CH3:32])[N:10]=1)=[CH:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 69370485HCID 69370485, compound

Product 1

HCID 69371258HCID 69371258, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazol-6-yl}-benzene-1,3-diamine (91 mg, 0.2 mmol) and pyridine (0.081 mL, 1.0 mmol) in CH2Cl2 (0.5 mL) cooled to −5° C. under an atmosphere of argon was added benzoyl chloride (0.028 mL, 0.24 mmol). After 0.5 h the reaction was quenched with saturated NaHCO3(aq) then extracted 2×5 mL CH2Cl2. The pooled organic material was washed with brine (5 mL), dried with Na2SO4, decanted and concentrated under reduced pressure to give an oil. The crude material was purified by silica gel chromatography (eluting with hexane:EtOAc 3:2) to give N-(3-{3-Styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazol-6-ylamino}-phenyl)-benzamide (108 mg, 96% yield). Rf sm 0.35, Rf p 0.44 (ethyl acetate hexane 1:1); FTIR (thin film) 3320, 2951, 2893, 1657, 1604, 1537, 1493, 1409, 1303, 1248, 1074 cm−1; LCMS (ESI) [M+H]/z Calc'd 561, Found 561. Anal. Calc'd: C, 72.82; H, 6.47; N, 9.99. Found: C, 72.33; H, 6.39; N, 9.81.

Workup

  1. customAfter 0.5 h the reaction was quenched with saturated NaHCO3(aq)
  2. extractionthen extracted 2×5 mL CH2Cl2
  3. washThe pooled organic material was washed with brine (5 mL)
  4. dry with materialdried with Na2SO4
  5. customdecanted
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil
  8. customThe crude material was purified by silica gel chromatography (eluting with hexane:EtOAc 3:2)

Sources & evidence

ORD record
ord-07227b009ee54124a0d0231f54079869
Source dataset
uspto-grants-2005_05
Patent number
US06891044B2

Reaction notes

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