Pyridine → HCID 69371258, compound

HRID 724385Notes

Reaction equation

HRID 724385 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-db27743a5369400c8447a31bd8f6bc5b
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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