Methyl iodide → HCID 72782509, compound

HRID 1987350Notes

Reaction equation

HRID 1987350 reaction equation
[CH3:1][C:2]1[C:3]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]2[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][O:29][CH3:30])=[CH:24][C:23]=2[CH2:31][OH:32])=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].CI.[CH2:37](Cl)Cl>C1COCC1.[Cl-].[Na+].O>[CH3:37][O:32][CH2:31][C:23]1[CH:24]=[C:25]([CH2:28][O:29][CH3:30])[CH:26]=[CH:27][C:22]=1[CH2:21][N:9]1[CH:8]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:13][CH2:12][CH2:11][CH:10]1[C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 67420308HCID 67420308, compound

Product 1

HCID 72782509HCID 72782509, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a cold (0° C.) solution of [2-(3,3″-Dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-5-methoxymethyl-phenyl]-methanol (0.085 g, 0.20 mmol) in THF (2 mL) was added a slurry of NaH (95% dry, 0.100 g, 4.17 mmol) in THF (2 mL) followed by neat MeI (0.25 mL, 4.02 mmol). The resultant mixture was stirred for 2.5 hours and treated with brine (5 mL) and CH2Cl2 (10 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (4×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (1 mm plate, 50:1:1 CH2Cl2—CH3OH—NH4OH) gave COMPOUND 55 (60 mg, 64%) as a colorless oil. 1H NMR (CDCl3) δ 1.65-1.73 (m, 3H), 2.00-2.07 (m, 1H), 2.20-2.41 (m, 8H), 3.21 (s, 6H), 3.56 (s, 2H), 3.97 (m, 2H), 4.18 (s, 2H), 4.22 (s, 2H), 6.77 (s,1H), 6.83-6.89 (m, 3H), 7.14-7.20 (m, 3H), 8.31 (d, 2H, J=3.6 Hz); 13C NMR (CDCl3) δ 19.22, 25.72, 28.37, 48.62, 57.85, 58.50, 66.60, 72.27, 74.68, 122.14, 125.94, 126.81, 129.51, 132.43, 135.29, 135.36, 138.11, 138.62, 146.56, 160.00; ES-MS m/z 446 (M+H). Anal. Calcd. For C28H35N3O2.0.3CH2Cl2: C, 72.16; H, 7.62; N, 8.92. Found: C, 71.88; H, 7.61; N, 8.95.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with CH2Cl2 (4×10 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification of the crude material by radial chromatography on silica gel (1 mm plate, 50:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-7c0bd9a1846c4842825bee4e9c6e7648
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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