Ethanesulfonyl chloride → HCID 46946630, compound

HRID 502226Notes

Reaction equation

HRID 502226 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:24][CH3:25])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][C:20]([F:23])([F:22])[F:21])[CH:11]=3)=[CH:4][CH:3]=1.[CH2:26]([S:28](Cl)(=[O:30])=[O:29])[CH3:27]>N1C=CC=CC=1.O>[C:17]([C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:19][C:20]([F:23])([F:21])[F:22])=[CH:13][CH:14]=2)[N:9]([CH2:24][CH3:25])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:28]([CH2:26][CH3:27])(=[O:30])=[O:29])=[CH:7][CH:6]=1)#[N:18]

Participants

5

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 59426292HCID 59426292, compound

Product 1

HCID 46946630HCID 46946630, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of the compound obtained in step C (31 mg, 0.1 mmol) in dry pyridine (1.0 mL) is added ethanesulfonyl chloride (14 μL, 0.15 mmol). The mixture is stirred at room temperature overnight and diluted with water (5 mL). The organic is extracted with DCM (5 mL) and washed with HCl (2N, 2×3 mL), water (2×4 mL) and brine (3 mL) and chromatographed (silica gel, EtOAc/DCM, 0.5/9.5) to provide the product, ethanesulfonic acid [4-(3-cyano-1-ethyl-6-trifluoromethoxyindol-2-yl)phenyl]amide (33 mg, 83%).

Workup

  1. extractionThe organic is extracted with DCM (5 mL)
  2. washwashed with HCl (2N, 2×3 mL), water (2×4 mL) and brine (3 mL)
  3. customchromatographed (silica gel, EtOAc/DCM, 0.5/9.5)

Sources & evidence

ORD record
ord-79fed7e612eb4372b2490b2529483d46
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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