Potassium tert-butoxide → HCID 69099792, compound

HRID 2251534Notes

Reaction equation

HRID 2251534 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]([C:10]1[CH:11]=[CH:12][C:13]([N:16]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)[CH2:17][CH2:18][C:19]2[CH:33]=[CH:32][C:22]([O:23][C:24]([CH3:31])([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=2)=[N:14][CH:15]=1)(=O)[CH3:8]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.C(O)(C)(C)C>[C:7]([C:10]1[CH:11]=[CH:12][C:13]([N:16]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:42])([F:44])[F:43])=[CH:37][CH:36]=2)[CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:23][C:24]([CH3:31])([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:32][CH:33]=2)=[N:14][CH:15]=1)([CH3:1])=[CH2:8]

Participants

6

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59643195HCID 59643195, compound

Product 1

HCID 69099792HCID 69099792, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyltriphenylphosphonium bromide (101 mg; 0.28 mmol) in 0.76 ml of THF was treated under nitrogen with potassium tert-butoxide (0.28 ml of a 1M solution in tert-butanol). After 10 minutes, ethyl 2-[4-(2-{(5-acetylpyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (100 mg; 0.19 mmol) was added. After 2 hours the reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The organic phase was dried over sodium sulfate and concentrated. Purification by flash chromatography using 10% ethyl acetate-hexane mixtures afforded ethyl 2-[4-(2-{(5-isopropenylpyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (30 mg; 30% yield).

Workup

  1. concentrationAfter 2 hours the reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-9c8be63b07474ba3b193410a9cf1da9f
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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