Methanesulfonyl chloride → HCID 69353580, compound

HRID 1827462Notes

Reaction equation

HRID 1827462 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11](O)[CH2:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][N:14]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.S(Cl)(C)(=O)=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[CH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][N:14]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178436305HCID 178436305, compound

Product 1

HCID 69353580HCID 69353580, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(6-Chloro-1H-indazol-3-yl)-2-(5-ethyl-pyridin-2-yl)-ethanol (232 mg, 0.60 mmol) in CH2Cl2 was added TEA (0.25 mL, 1.81 mmol) and mesyl chloride (0.070 mL, 0.90 mmol). The reaction was stirred for 30 minutes, and then DBU (2 mL) was added. The reaction was refluxed for 18 hours and then quenched with 40 mL of 1 N citric acid. The layers were separated, and the aqueous was extracted with 20 mL CH2Cl2. The combined organics were dried over Na2SO4, filtered, and concentrated by rotary evaporation. Purification by chromatography (12 g silica gel, 50–70% EtOAc/hexanes) yielded the desired compound (135 mg, 71%).

Workup

  1. temperatureThe reaction was refluxed for 18 hours
  2. customquenched with 40 mL of 1 N citric acid
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with 20 mL CH2Cl2
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customPurification by chromatography (12 g silica gel, 50–70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6bf77448e5734500a5aa2f2c2616e2a3
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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