Acetic Anhydride → HCID 57934161, compound

HRID 1950014Notes

Reaction equation

HRID 1950014 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:16]([F:29])[CH:15]=1)[C:10](=[O:12])[CH3:11].BrC1C=C[C:34]([O:37]C)=[CH:33]C=1N(CC1C=CC(OCCN2CCCCC2)=C(F)C=1)C(=O)C.C(OC(=O)C)(=O)C.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:10]([N:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:16]([F:29])[CH:15]=1)[C:3]1[CH:4]=[C:5]([O:8][C:34](=[O:37])[CH3:33])[CH:6]=[CH:7][C:2]=1[Br:1])(=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 57934361HCID 57934361, compoundHCID 66626955HCID 66626955, compound

Product 1

HCID 57934161HCID 57934161, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the total amount of N-(2-bromo-5-hydroxyphenyl)-N-[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]acetamide crude product, which was synthesized from N-(2-bromo-5-methoxyphenyl)-N-[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]acetamide (380 mg) synthesized according to an analogous synthetic method to Example 364 described below, were added pyridine (2 ml) and acetic anhydride (2 ml), and the solution was stirred for 1 hour at room temperature. To the reaction mixture was added a saturated aqueous solution of sodium bicarbonate, the solution was extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform-methanol system) to provide the title compound (350 mg).

Workup

  1. customsynthesized
  2. extractionthe solution was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol system)

Sources & evidence

ORD record
ord-fd154cd48e5a48918b3d03c2fd7748b2
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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