Pyridine → HCID 6461680, compound

HRID 2184934Notes

Reaction equation

HRID 2184934 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH2:16])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 85883-Amino-9-ethylcarbazoleHCID 31297Methanesulfonyl chloride

Product 1

HCID 6461680HCID 6461680, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 9-Ethyl-9H-carbazol-3-ylamine (210 mg, 1 mmol) and pyridine (105 μl, 1.3 mmol) in CH2Cl2 (8 ml) at room temperature was added methanesulfonyl chloride (85 μl, 1.1 mmol). After stirring overnight the reaction mixture was diluted with CH2Cl2 and washed with saturated aq. NaHCO3 and brine, then the organic layer dried (Na2SO4) and concentrated to afford the crude product. Chromatographic purification (silica, CH2Cl2) afforded the desired product as a pale yellow solid (203 mg, 70% yield).

Workup

  1. washwashed with saturated aq. NaHCO3 and brine
  2. dry with materialthe organic layer dried (Na2SO4)
  3. concentrationconcentrated
  4. customto afford the crude product
  5. customChromatographic purification (silica, CH2Cl2)

Sources & evidence

ORD record
ord-bd2f5eb2db784947864703cb5067ecad
Source dataset
uspto-grants-2002_06
Patent number
US06399631B1

Reaction notes

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