Methyl iodide → 4-[1-(6-Bromopyridin-2-yl)-2-methoxyethyl]morpholine

HRID 385993Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([CH:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH2:9][OH:10])[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:20].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH2:9][O:10][CH3:20])[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(6-Bromopyridin-2-yl)-2-morpholin-4-ylethanol (Example 141, Step 1) (1 g, 3.48 mmol) was taken up in THF (7 mL) and cooled to 0° C. Sodium hydride (0.153 g, 3.83 mmol) was added and the suspension stirred at 0° C. for 5 minutes. A solution of iodomethane (0.240 mL, 3.83 mmol) in THF (3 mL) was added and the reaction mixture stirred at 0° C. for 30 minutes. Saturated NH4Cl was added and the reaction mixture was extracted with EtOAc (2×). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel column chromatography (40-100% EtOAc-hexanes) gave the title compound as a yellow oil.

Workup

stirringthe reaction mixture stirred at 0° C. for 30 minutes
extractionthe reaction mixture was extracted with EtOAc (2×)
dry with materialThe combined organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the residue by silica gel column chromatography (40-100% EtOAc-hexanes)

Sources & evidence

ORD record: ord-d41bcdab599d48d2a9dab747221e7949
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367706B2

Reaction notes

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