Isopropyltriphenylphosphonium bromide → HCID 69099725, compound

HRID 2251536Notes

Reaction equation

HRID 2251536 reaction equation
[Br-].[CH:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:4])[CH3:3].C([Li])CCC.[CH:29]([C:31]1[CH:32]=[CH:33][C:34]([N:37]([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([O:62][C:63]([F:66])([F:65])[F:64])=[CH:58][CH:57]=2)[CH2:38][CH2:39][C:40]2[CH:54]=[CH:53][C:43]([O:44][C:45]([CH3:52])([CH3:51])[C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:42][CH:41]=2)=[N:35][CH:36]=1)=O>C1COCC1.CCCCCC>[CH3:52][C:45]([O:44][C:43]1[CH:53]=[CH:54][C:40]([CH2:39][CH2:38][N:37]([C:34]2[CH:33]=[CH:32][C:31]([CH:29]=[C:2]([CH3:4])[CH3:3])=[CH:36][N:35]=2)[CH2:55][C:56]2[CH:61]=[CH:60][C:59]([O:62][C:63]([F:65])([F:64])[F:66])=[CH:58][CH:57]=2)=[CH:41][CH:42]=1)([CH3:51])[C:46]([O:48][CH2:49][CH3:50])=[O:47]

Participants

6

Reactant 3

HCID 2795292Isopropyltriphenylphosphonium bromideHCID 59643273HCID 59643273, compoundHCID 178418339Butyllithium

Product 1

HCID 69099725HCID 69099725, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of isopropyltriphenylphosphonium bromide (326 mg; 0.75 mmol) in 1.5 ml of dry THF was treated in an ice bath, under nitrogen, with n-butyl lithium (0.425 ml of a 1.6M solution in hexane; 0.68 mmol), dropwise. After stirring for 15 minutes, this mixture was added, via syringe, into an ice-cold solution of ethyl 2-[4-(2-{(5-formylpyridin-2-yl)[4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (200 mg; 0.38 mmol) in 2 ml of dry THF. After stirring at rt overnight, the reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and concentrated. Purification by radial chromatography using ethyl acetate-hexane mixtures (5–20% gradient) afforded ethyl 2-methyl-2-[4-(2-{[5-(2-methylprop-1-enyl)pyridin-2-yl][4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]propanoate (70 mg; 33% yield).

Workup

  1. stirringAfter stirring at rt overnight
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by radial chromatography

Sources & evidence

ORD record
ord-f08de614410e444ba5cbf1e46474f706
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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