Sodium hydride → HCID 15712518, compound

HRID 2081211Notes

Reaction equation

HRID 2081211 reaction equation
[H-].[Na+].[F:3][C:4]1[C:12]2[N:11]([CH2:13][O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]3[CH2:22][CH2:23][NH:24][C:25](=[O:26])[C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1.Cl[CH2:28][C:29]1[N:30]=[CH:31][N:32](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:33]=1[CH3:34].C(=O)(O)[O-].[Na+]>COCCOC.C(O)(=O)C.O>[F:3][C:4]1[C:12]2[N:11]([CH2:13][O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]3[CH2:22][CH2:23][N:24]([CH2:28][C:29]4[N:30]=[CH:31][NH:32][C:33]=4[CH3:34])[C:25](=[O:26])[C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 110469654-(Chloromethyl)-5-methyl-1-trityl-1H-imidazoleHCID 15712510HCID 15712510, compound

Product 1

HCID 15712518HCID 15712518, compoundYield 306%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (60% dispersion in oil; 28 mg) was added to a stirred solution of 6-fluoro-2,3,4,5-tetrahydro-5-[(phenylmethoxy)methyl]-1H-pyrido[4,3-b]indol-1-one (190 mg) in dry DME (10 ml). The mixture was heated at 50° for 6 h then treated with 4-(chloromethyl)-5-methyl-1-(triphenylmethyl) -1H-imidazole (261 mg) and stirring was continued under nitrogen for 18 h. Water (2 ml) and acetic acid (2 ml) were added and the solution was heated at reflux for 2.5 h. The solution was poured into 8% sodium bicarbonate solution (50 ml) and extracted with dichloromethane (3×25 ml). The combined, dried organic extracts were evaporated to give an oil (ca. 750 mg) which was purified by FCC eluting with System A (200:10:1) to give the title compound (188 mg), t.l.c (System A, 200:10:1) Rf 0.33.

Workup

  1. temperatureThe mixture was heated at 50° for 6 h
  2. temperaturethe solution was heated
  3. temperatureat reflux for 2.5 h
  4. extractionextracted with dichloromethane (3×25 ml)
  5. customdried organic extracts were evaporated

Sources & evidence

ORD record
ord-a493e562eef34474b19e19e1679b5f4c
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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