Sodium Iodide → HCID 16660201, compound

HRID 2264703Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.Cl[CH2:22][CH2:23][CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.[H-].[Na+].[I-].[Na+]>CN(C)C=O>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:22][CH2:23][CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:18][CH:19]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

Conditions

Temperature: 70 °C

Procedure

4-[2-(2-Methoxyethyl)indol-1-yl]phenol (0.39 mmol) was dissolved in N,N-dimethylformamide (4 mL), and 1-(3-chloropropyl)pyrrolidine (58 mg, 0.39 mmol), sodium hydride (19 mg, 60% dispersion in mineral oil, 0.47 mmol), and sodium iodide (59 mg, 0.39 mmol) were added. The reaction was heated at 70° C. for 1.5 hours, then carefully quenched with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by SiO2 chromatography to give 70 mg of the desired product. LC-MS (C24H30N2O2 calc'd 378) m/z 379 (M+H); 1H NMR (300 MHz, CDCl3) d 7.60-7.56 (m, 1H), 7.25-7.21 (m, 2H), 7.10-7.00 (m, 5H), 6.45 (s, 1H), 4.11 (t, J=6.3 Hz, 2H), 3.57 (t, J=7.2 Hz, 2H), 3.30 (s, 3H), 2.89 (t, J=7.2 Hz, 2H), 2.74 (t, J=7.5 Hz, 2H), 2.65 (m, 4H), 2.16-2.05 (m, 2H), 1.90-1.81 (m, 4H).

Workup

customcarefully quenched with saturated sodium bicarbonate solution
extractionThe mixture was extracted with ethyl acetate
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by SiO2 chromatography

Sources & evidence

ORD record: ord-ba2053802a9f45cdbc84dc4996a95141
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855224B2

Reaction notes

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