Ammonium Chloride → HCID 22465357, compound

HRID 1935749Notes

Reaction equation

HRID 1935749 reaction equation
C([Mg]Br)C.I[C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1.[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39](=[O:46])[CH2:38]2)=[CH:33][CH:32]=1.[Cl-].[NH4+]>C(OCC)C.C(Cl)Cl>[F:30][C:31]1[CH:32]=[CH:33][C:34]([CH:37]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]([C:6]3[N:7]=[CH:8][N:9]([C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:10]=3)([OH:46])[CH2:38]2)=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 6182524-Iodo-1-tritylimidazoleHCID 30177883-(4-Fluorophenyl)-2,3-dihydro-1H-inden-1-oneHCID 178418443HCID 178418443, compound

Product 1

HCID 22465357HCID 22465357, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A 3.0 M solution of ethylmagnesium bromide (5.9 ml, 0.0177 mol) in diethyl ether was added to a solution of 4-iodo-1-trityl-1H-imidazole (7.22 g, 0.0165 mol, prepared according to K. L. Kirk J. Heterocycl. Chem. 22 (1985) 57) in 70 ml of dry methylene chloride at ambient temperature. After one hour, a solution of 3-(4-fluorophenyl)indan-1-one (2.00 g, 0.00884 mol) in 6 ml of dry methylene chloride was added and stirring was continued for 45 hr. Saturated ammonium chloride solution was added to quench the reaction. The methylene chloride phase was separated and the aqueous phase was extracted twice with methylene chloride. The combined organic extracts were washed with brine, dried and concentrated. The crude 3-(4-fluorophenyl)-1-(1-trityl-1H-imidazol-4-yl)indan-1-ol was purified by flash chromatography using methylene chloride as an eluent.

Workup

  1. waitwas continued for 45 hr
  2. customto quench
  3. customthe reaction
  4. customThe methylene chloride phase was separated
  5. extractionthe aqueous phase was extracted twice with methylene chloride
  6. washThe combined organic extracts were washed with brine
  7. customdried
  8. concentrationconcentrated
  9. customThe crude 3-(4-fluorophenyl)-1-(1-trityl-1H-imidazol-4-yl)indan-1-ol was purified by flash chromatography

Sources & evidence

ORD record
ord-4c561bafa41b4e76a1352a4c9a4b89a4
Source dataset
uspto-grants-2002_05
Patent number
US06388090B2

Reaction notes

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