Lithium iodide → HCID 22036173, compound

HRID 1789663Notes

Reaction equation

HRID 1789663 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[CH2:8][CH2:9][CH2:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:4][C:3]=1[O:27]C.[I-].[Li+]>N1C(C)=CC(C)=CC=1C>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:17][CH:16]=2)[CH2:8][CH2:9][CH2:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:4][C:3]=1[OH:27]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 22036202HCID 22036202, compound

Product 1

HCID 22036173HCID 22036173, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To 694 mg (1.67 mmol) of (4-fluoro-3-methoxy-benzyl)-(4-methanesulfonyl-phenyl)-(3-methanesulfonyl-propyl)-amine, prepared following the method of Example 5 but replacing 3-pyridinecarboxaldehyde with 4-fluoro-3-methoxybenxaldehyde, dissolved in 3 mL of 2,4,6-collidine was added 402 mg (3.01 mmol) lithium iodide. The mixture was heated to 150 degrees for 3 hrs, cooled to room temperature, and partitioned between ethyl acetate and 1 N HCl. Upon drying over magnesium sulfate and concentration, column chromatography, eluting with acetone/dichloromethane, provided 169 mg of 2-fluoro-5-{[(4-methanesulfonyl-phenyl)-(3-methanesulfonyl-propyl)-amino]-methyl}-phenol; (m+H)+=401.

Workup

  1. temperatureThe mixture was heated to 150 degrees for 3 hrs
  2. custompartitioned between ethyl acetate and 1 N HCl
  3. dry with materialUpon drying over magnesium sulfate and concentration, column chromatography
  4. washeluting with acetone/dichloromethane

Sources & evidence

ORD record
ord-63953ee471764db6b6b59ef0e61ecf7b
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

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