Triphenylphosphine → 6-Bromo-7-methoxy-4-(4-(2-pyrrolidin-1-yl-ethoxy)-benzyl)-3-(4-trifluoromethyl-phenyl)-chromen-2-one

HRID 1296697Notes

Reaction equation

HRID 1296697 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][C:7](=[O:14])[C:6]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)=[C:5]2[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:53][CH2:54][N:55]1[CH2:59][CH2:58][CH2:57][CH2:56]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][C:7](=[O:14])[C:6]([C:15]1[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:19][CH:20]=1)=[C:5]2[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:53][CH2:54][N:55]2[CH2:59][CH2:58][CH2:57][CH2:56]2)=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 762881-PyrrolidineethanolHCID 589131126-Bromo-4-(4-hydroxy-benzyl)-7-methoxy-3-(4-trifluoromethyl-phenyl)-chromen-2-one

Product 1

HCID 589131386-Bromo-7-methoxy-4-(4-(2-pyrrolidin-1-yl-ethoxy)-benzyl)-3-(4-trifluoromethyl-phenyl)-chromen-2-oneYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-4-(4-hydroxy-benzyl)-7-methoxy-3-(4-trifluoromethyl-phenyl)-chromen-2-one (0.70 g, 1.4 mmol) and triphenylphosphine (0.73 g, 2.8 mmol) in THF (40 mL) were sequentially added 1-(2-hydroxylethyl)pyrrolidine (0.65 mL, 5.6 mmol) and diisoproyl azodicaroxylate (0.55 mL, 2.8 mmol). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was poured into water and extracted with EtOAc. Organic extracts were combined and washed with water and saturated sodium chloride in succession, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification using silica gel flash column chromatography (10% methanol in CH2Cl2) provided the title compound as a solid (0.44 g, 53%). MS (ESI) m/z 602.3 (M+1)+, 604.3 (M+1+2)+.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with water and saturated sodium chloride in succession
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification

Sources & evidence

ORD record
ord-00df6109d536422698ad73f4003db43e
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

Loading…