Imidazole → HCID 21949785, compound

HRID 2114643Notes

Reaction equation

HRID 2114643 reaction equation
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[Cl:27][C:28]1[CH:29]=[C:30]([CH:51]=[C:52]([Cl:54])[CH:53]=1)[O:31][C:32]1[C:33]([CH2:49][CH3:50])=[N:34][N:35]([CH2:39][CH2:40][NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:36]=1[CH2:37]O>ClCCl>[Br:1][CH2:37][C:36]1[N:35]([CH2:39][CH2:40][NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[N:34]=[C:33]([CH2:49][CH3:50])[C:32]=1[O:31][C:30]1[CH:29]=[C:28]([Cl:27])[CH:53]=[C:52]([Cl:54])[CH:51]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 21949866HCID 21949866, compound

Product 1

HCID 21949785HCID 21949785, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Bromine (160 μl, 3.12 mmol) was added dropwise to a stirred solution of triphenylphosphine (820 mg, 3.12 mmol) and imidazole (213 mg, 3.12 mmol) in dichloromethane (15 ml) at room temperature under nitrogen. A solution of the alcohol of Example 135 (1.12 g, 2.60 mmol) in dichloromethane (5 ml) was then added to the reaction. The reaction was stirred at room temperature for 2 hours, diluted with dichloromethane (50 ml), washed with brine (20 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2, by volume) to provide the title compound (969 mg) as a white foam.

Workup

  1. washwashed with brine (20 ml)
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2, by volume)

Sources & evidence

ORD record
ord-4255f9f510b047beb990075d6ee96fe1
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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