Sodium hydride → HCID 54556570, compound

HRID 1463688Notes

Reaction equation

HRID 1463688 reaction equation
[N:1]1[C:13]2[CH2:12][C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[N:14]1[CH:19]=[CH:18][C:17]([CH2:20]Cl)=[CH:16][CH:15]=1.[H-].[Na+].[N:24]1[C:36]2C[C:34]3[C:29](=[CH:30]C=C[CH:33]=3)[C:28]=2C=CN=1>O1CCCC1.C(OCC)(=O)C.CO.C1C=CC=CC=1>[N:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:12]2([CH2:30][C:29]3[CH:34]=[CH:33][N:24]=[CH:36][CH:28]=3)[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[C:5]3[C:13]2=[N:1][CH:2]=[CH:3][CH:4]=3)=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 745714-(Chloromethyl)pyridineHCID 64105969H-Indeno(2,1-c)pyridazineHCID 12433675HCID 12433675, compound

Product 1

HCID 54556570HCID 54556570, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

Following the alkylation procedure described in Example 608, Part D, 2.0 g (12 mmole) of 1,5-diazafluorene, 4.68 g (29 mmole) of 4-picolylchloride, 1.44 g (30 mmole) of 50% sodium hydride were heated at 55° in 10 ml tetrahydrofuran and 25 ml benzene until TLC (ethyl acetate-methanol-90:10) showed appearance of product (Rf 0.065) and disappearance of starting diazafluorene (Rf 0.28). Crude product triturated with ether to yield 2.90 g, m.p. 133°-137°. This was flash chromatographed with ethyl acetate and recrystallized from benzene using charcoal to decolorize. Yield 2.4 g, m.p. 139.8°-140.9°. Rf 0.16 (ethyl acetate-methanol 90:10). NMR (200 MHz,CDCl3) δ 3.397-3.718(dd,4H,(--CH2 --pyridyl); 6.450-6.475(d,4H,β-pyridyls); 7.240-7.324(m,2H,the 3- and 7- H's of the 1,5-diazafluorene, each meta to one of the nitrogens); 7.802-7.808(d,1H,8-H of diazafluorene); 7.879-7.885(d,1H,4-H of diazafluorene); 8.097-8.122 (d,4H,α-pyridyls); 8.451-8.476(d,1H,2-H of diazafluorene); 8.741-8.763(d,1H,6-H of diazafluorene).

Workup

  1. customCrude product triturated with ether
  2. customto yield 2.90 g, m.p. 133°-137°
  3. customThis was flash chromatographed with ethyl acetate
  4. customrecrystallized from benzene

Sources & evidence

ORD record
ord-535bb34964a347bd8aa82061558af50d
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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