Pyridine → 4-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzyl bromide

HRID 1007479Notes

Reaction equation

HRID 1007479 reaction equation
[Br-:1].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:22]([C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([O:34][C:35]3[C:42]([C:43]([F:46])([F:45])[F:44])=[CH:41][C:38]([CH2:39]O)=[CH:37][C:36]=3[C:47]([F:50])([F:49])[F:48])[CH:32]=2)[NH:27][CH:26]=1)([CH3:24])[CH3:23].N1C=CC=CC=1>C(#N)C>[CH:22]([C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([O:34][C:35]3[C:42]([C:43]([F:46])([F:45])[F:44])=[CH:41][C:38]([CH2:39][Br:1])=[CH:37][C:36]=3[C:47]([F:50])([F:49])[F:48])[CH:32]=2)[NH:27][CH:26]=1)([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12890784Triphenylphosphane dibromideHCID 601106964-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzyl alcohol

Product 1

HCID 226697784-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzyl bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.273 g (3.02 mmol) of triphenylphosphine dibromide are added under argon in portions at 0° C. to a solution of 0.97 g (2.32 mmol) of benzyl alcohol derivative from Example VI in 15 ml of acetonitrile and 0.3 ml (3.72 mmol) of pyridine. After 15 minutes the cooling bath is removed and the mixture is stirred for 2 hours at room temperature. The reaction solution is concentrated in vacuo, and the residue is dissolved in a little toluene and purified by chromatography on silica gel 60 by means of toluene.

Workup

  1. customAfter 15 minutes the cooling bath is removed
  2. concentrationThe reaction solution is concentrated in vacuo
  3. dissolutionthe residue is dissolved in a little toluene
  4. custompurified by chromatography on silica gel 60 by means of toluene

Sources & evidence

ORD record
ord-afe37500c08f41e08a7773c62a994d7e
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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