Pyrrolidine → Methyl 2-(3-(pyrrolidin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxylate

HRID 415220Notes

Reaction equation

HRID 415220 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[O:10][C:11]3[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:6]=[CH:7][CH:8]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>C(O)C>[N:22]1([CH2:2][C:3]2[CH:4]=[C:5]([C:9]3[O:10][C:11]4[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)[CH:6]=[CH:7][CH:8]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 66620978Methyl 2-(3-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 66621401Methyl 2-(3-(pyrrolidin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxylateYield 120.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-(3-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate (70 mg, 0.2 mmol) and pyrrolidine (56.8 mg, 0.8 mmol) were added to ethanol (30 mL) and the mixture was stirred at room temperature for 1 hr. The resulting mixture was evaporated under reduced pressure to obtain methyl 2-(3-(pyrrolidin-1ylmethyl)phenyl)benzo[d]oxazole-7-carboxylate (81 mg, yield 88%). LC-MS (ESI) m/z 337 [M+1]+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ef223013e9144a978936ec83d59c6e69
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…