Hydrochloric Acid → HCID 69017273, compound

HRID 1455082Notes

Reaction equation

[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([OH:17])[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.[OH-].[K+].[I-].[K+].Cl>CS(C)=O>[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[CH:13]=3)[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

2-Phenylchroman-6-ol (598 mg), 3-bromopyridine (500 mg), potassium hydroxide (322 mg) and potassium iodide were placed in a flask with dry DMSO (10 ml). The reaction mixture was stirred at 120° C. for 3.5 hours. After cooling to room temperature 1M HCl-solution was added and the mixture was extracted wit dichloromethane. The combined organig extracts were washed with 1 M HCl-solution, then with water and brine and dried. 3-(2-Phenylchroman-6-yloxy)pyridine was purified by column chromatography using heptane-ethyl acetate as an eluant. 1H NMR (400 MHz, d6-CDCl3+MeOH) δ: 8.31 (s, 1H), 8.24 (dd, 1H, J 3.8, 1.9 Hz), 7.45-7.25 (m, 7H), 6.87 (d, 1H, J 8.6 Hz), 6.83 (dd, 1H, J 8.6, 2.6 Hz), 6.81 (d, 1H, J 2.6 Hz), 5.07 (dd, 1H, J 10.1, 2.3 Hz), 2.98 (m, 1H), 2.78 (m, 1H), 2.23 (m, 1H), 2.12 (m, 1H).

Workup

additionwas added
extractionthe mixture was extracted wit dichloromethane
washThe combined organig extracts were washed with 1 M HCl-solution
dry with materialwith water and brine and dried
custom3-(2-Phenylchroman-6-yloxy)pyridine was purified by column chromatography

Sources & evidence

ORD record: ord-2ca5703d82ba4cf58177286dab27d548
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482340B2

Reaction notes

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