Water → HCID 57722873, compound

HRID 222291Notes

Reaction equation

HRID 222291 reaction equation
OC1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=2)[CH:6]=[CH:5][C:4]2C=C[C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][C:3]1=2.[H-].[Na+].[CH3:30]I.O.[CH2:33]1[CH2:37][O:36][CH2:35][CH2:34]1>CCOC(C)=O>[CH3:35][O:36][CH:37]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=2)[CH:6]=[CH:5][C:4]2[CH:3]=[CH:22][C:21]([N:23]([CH3:30])[S:24]([CH3:27])(=[O:26])=[O:25])=[CH:34][C:33]1=2

Participants

7

Reactant 5

HCID 962WaterHCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 53309969HCID 53309969, compound

Product 1

HCID 57722873HCID 57722873, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-(5-hydroxy-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)methanesulfonamide (30 mg, 0.079 mmol) in THF (3 mL) was added NaH (60%, 10 mg, 0.25 mmol) at 0° C. After 10 min, MeI (50 uL, 0.80 mmol) was added, and the resultant mixture was allowed to stir at room temperature for 4 h. The reaction mixture was treated with water, diluted with EtOAc, washed with brine, dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 8.71 (s, 1H); 8.07 (s, 1H); 7.19-7.60 (m, 10H); 4.71 (br s, 1H); 3.50 (br s, 3H); 3.28 (s, 3H); 2.79 (s, 3H). LRMS (APCI) calc'd for (C23H23N2O3S) [M+H]+, 407.1; found 407.2.

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-663c96e424104745bc2f82b43735cc58
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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