Ethanesulfonylchloride, 2-chloro- → ethenesulfonic acid [4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]amide
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:21][CH3:22])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:4][CH:3]=1.Cl[CH2:24][CH2:25][S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1>[C:17]([C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[CH:13][CH:14]=2)[N:9]([CH2:21][CH3:22])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:26]([CH:25]=[CH2:24])(=[O:28])=[O:27])=[CH:7][CH:6]=1)#[N:18]Participants
4
Procedure
A solution of 2-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile, prepared by example 1Ga step B, (0.82 mg, 2.82 mmol), in pyridine (10 mL) is treated dropwise with chloroethyl sulfonylchloride (0.38 mL, 3.66 mmol) at room temperature. After stirring for 4 h, the reaction mixture is quenched with ice-water and enough 6N HCl is added until the pH is lowered to 2. The suspension is extracted with hot EtOAc (3×). The organic phases are then washed sequentially with 1N HCl, H2O and saturated NaCl and dried and concentrated to give ethenesulfonic acid [4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]amide as a pale orange solid which is used directly in the next step without further purification.
Workup
- customthe reaction mixture is quenched with ice-water and enough 6N HCl
- additionis added until the pH
- extractionThe suspension is extracted with hot EtOAc (3×)
- washThe organic phases are then washed sequentially with 1N HCl, H2O and saturated NaCl
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bcc171ca88914ba18f195c666ce3a142
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07868037B2
Reaction notes
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