Ethanesulfonyl chloride → HCID 46946630, compound

HRID 1009638Notes

Reaction equation

HRID 1009638 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-6feecf1b65df4d6ca7cb1ecda7adea18
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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