Triphenylphosphine → Ethyl 5-bromo-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylate

HRID 513202Notes

Reaction equation

HRID 513202 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[F:16][C:17]([F:30])([F:29])[O:18][C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25]O)=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:25][CH2:24][O:23][C:22]1[CH:21]=[CH:20][C:19]([O:18][C:17]([F:16])([F:29])[F:30])=[CH:28][CH:27]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 259091Ethyl 5-Bromoindole-2-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 211086172-[4-(Trifluoromethoxy)phenoxy]ethanol

Product 1

HCID 71212593Ethyl 5-bromo-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylateYield 53.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 5-bromo-1H-indole-2-carboxylate (1.7 g, 6.3 mmol), 2-[4-(trifluoromethoxy)phenoxy]ethanol (1.7 g, 7.6 mmol) and triphenylphosphine (3.3 g, 12.7 mmol) in toluene (20 ml) was added DIAD (1.85 ml, 9.5 mmol) dropwise at 0° C. The mixture was left to warm up to RT and stirred overnight. The mixture was then concentrated in vacuo. The residue was purified on silica gel (0-20% EtOAc in hexanes) to yield the title product (1.6 g).

Workup

  1. waitThe mixture was left
  2. concentrationThe mixture was then concentrated in vacuo
  3. customThe residue was purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8d0f983731fd41b9bce3314c0501cbf9
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

Loading…