4-Toluenesulfonyl chloride → HCID 58999615, compound

HRID 1593621Notes

Reaction equation

HRID 1593621 reaction equation
C(O[C:4]([CH:6]1[CH2:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=3)[NH:10][C:9]=2[CH2:8][CH2:7]1)=[O:5])C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1>[F:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]1[CH2:8][CH2:7][CH:6]([CH2:4][O:5][S:26]([C:23]3[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=3)(=[O:28])=[O:27])[CH2:18][C:17]2=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 108582426-FLUORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-3-CARBOXYLIC ACID ETHYL ESTER2×

Product 1

HCID 58999615HCID 58999615, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of (6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methanol (compound IV of Example 2) (5.975 g, 0.0272 mol) in anhydrous pyridine (15 mL) was cooled in ice bath and treated dropwise under vigorous stirring with an ice cold solution of para-toluenesulfonyl chloride (6.17 g) in anhydrous pyridine (10 mL). After stirring for one hour in the cold, the mixture was placed overnight in the refrigerator. It was then quenched with water (100 mL) under stirring and cooling. After 30 minutes the mixture was extracted with ethyl acetate (3×100 mL). The extracts were washed with cold 3N sulfuric acid (100 mL), water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate and evaporated to dryness. The crude material (light brown foam, 9.827 g) was used as such in the next step. MS (ES): [M−H]− @m/z 372.1.

Workup

  1. additiontreated dropwise
  2. waitwas placed overnight in the refrigerator
  3. customIt was then quenched with water (100 mL)
  4. stirringunder stirring
  5. temperaturecooling
  6. extractionAfter 30 minutes the mixture was extracted with ethyl acetate (3×100 mL)
  7. washThe extracts were washed with cold 3N sulfuric acid (100 mL), water (100 mL) and brine (100 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-aab7483971b241cf88c7fd562c1ad513
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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