Dichloromethane → HCID 67422830, compound

HRID 1987348Notes

Reaction equation

HRID 1987348 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:5]=1[CH2:12][N:13]1[CH:18]([C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:17][CH2:16][CH2:15][CH:14]1[C:26]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=1.[H-].[Na+].[C:36]([O-])(O)=O.[Na+].C(Cl)Cl>C1COCC1>[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([CH2:10][O:11][CH3:36])[CH:7]=[CH:6][C:5]=1[CH2:12][N:13]1[CH:14]([C:26]2[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:15][CH2:16][CH2:17][CH:18]1[C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 67421332HCID 67421332, compound

Product 1

HCID 67422830HCID 67422830, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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-hydroxymethyl-benzoic acid methyl ester (0.290 g, 0.65 mmol) in THF (3 mL) was added a slurry of NaH (95% dry, 0.105 g, 4.38 mmol) in THF (10 mL) followed by neat Mel (0.40 mL, 6.43 mmol). The resultant mixture was stirred for 3 hours and treated with saturated aqueous NaHCO3 (15 mL) and CH2Cl2 (50 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2—CH3OH—NH4OH) gave COMPOUND 54 (239 mg, 80%) as a white solid. 1H NMR (CDCl3) δ 1.63-1.69 (m, 3H), 2.04-2.08 (m, 1H), 2.30-2.48 (m, 8H), 3.24 (s, 3H), 3.80 (s, 3H), 3.95 (s, 2H), 4.13 (d, 2H, J=11.7 Hz), 4.23 (s, 2H), 6.82 (dd, 2H, J=4.5, 7.5 Hz), 7.06-7.22 (m, 4H), 7.61 (d, 1H, J=7.8 Hz), 8.25 (d, 2H, J=4.5 Hz); 13C NMR (CDCl3) δ 19.31, 25.55, 28.99, 50.64, 51.97, 58.01, 66.99, 74.20, 122.01, 127.92, 128.41, 130.02, 131.46, 131.98, 134.84, 138.05, 143.31, 146.84, 159.84, 167.91; ES-MS m/z 460 (M+H). Anal. Calcd. For C28H33N3O3: C, 73.18; H, 7.24; N, 9.14. Found: C, 73.07; H, 7.15; N, 9.16.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with CH2Cl2 (3×15 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-c91e8e71e8734b77a329d9deeaa2d3c6
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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