Pyridine → HCID 68864225, compound

HRID 1725910Notes

Reaction equation

HRID 1725910 reaction equation
C[C:2]1[C:3]([NH2:15])=[C:4]([C:12]([OH:14])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24].N1C=CC=C[CH:28]=1>>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH:15][C:3]1[CH:2]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:12]([O:14][CH3:28])=[O:13])(=[O:25])=[O:24]

Participants

4

Reactant 3

HCID 1049PyridineHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 68862597HCID 68862597, compound

Product 1

HCID 68864225HCID 68864225, compound

Procedure

A solution of Example 133A (6.97 g, 34.7 mmol) in pyridine (70 mL) was treated with 2-fluorobenzenesulfonyl chloride (7.86 g, 40.4 mmol), stirred for 16 hours at ambient temperature, concentrated, diluted with 1M NaHSO4, and extracted with dichloromethane. The extract was dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product (6.04 g). MS (ESI(+)) m/e 360 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additiondiluted with 1M NaHSO4
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-346da9edf1dd4d4597f2453456f62d24
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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