Methyl iodide → HCID 18723511, compound

HRID 842231Notes

Reaction equation

HRID 842231 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([N:12]2[CH2:16][CH:15]([C:17]([F:20])([F:19])[F:18])[CH:14]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:13]2)=[O:11])[CH:3]=[CH:2]1.[CH2:35]1OCCOCCOCCOCCOCCOC1.CC([O-])(C)C.[K+].CI>CCOCC>[CH3:35][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([N:12]2[CH2:16][CH:15]([C:17]([F:19])([F:20])[F:18])[CH:14]([CH2:21][N:22]3[CH2:23][CH2:24][CH:25]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[CH2:26][CH2:27]3)[CH2:13]2)=[O:11])[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2855718-Crown-6HCID 18723510HCID 18723510, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18723511HCID 18723511, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 0.033 g (0.07 mmol) of 1-(7-indolecarbonyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(trifluoromethyl)pyrrolidine and 0.022 g (0.084 mmol) of 18-Crown-6 ether in 2 mL of ether at rt was added 0.084 mL of KOt-Bu (1M in t-BuOH). After stirring for 5 min, 0.006 mL (0.098 mmol) of MeI was added and the reaction was stirred for 1 h. The reaction mixture was concentrated and the residue was purified by chromatography (silica, acetone:hexanes, 1:3) to give the title compound. 1H NMR (CDCl3) δ (key peaks) 7.68-7.70 (m, 1H), 7.10-7.21 (m, 4H), 7.06 (t, 1H, J=3.0 Hz), 6.97-7.03 (m, 2H), 6.55 (d, 1H, J=3.0 hz); Mass Spectrum (ESI) m/e 488 (M+1).

Workup

  1. stirringthe reaction was stirred for 1 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by chromatography (silica, acetone:hexanes, 1:3)

Sources & evidence

ORD record
ord-d4a806eed7bb4ef8b9a6ae25afe931d7
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

Loading…