Sulfuryl chloride → 4-Chloro-5-[(phenylmethyl)oxy]-1-(phenylsulfonyl)-1H-indole-2-carbaldehyde
Reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:13]([CH:27]=[O:28])=[CH:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:32])(=O)=O>CC(O)=O.C(Cl)Cl>[Cl:32][C:10]1[C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[C:13]([CH:27]=[O:28])[N:14]2[S:18]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)(=[O:19])=[O:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-[(phenylmethyl)oxy]-1-(phenylsulfonyl)-1H-indole-2-carbaldehyde (3.22 g, 8.22 mmol) in 1:1 AcOH—CH2Cl2 (140 mL) was added sulfuryl chloride (1.24 g, 9.19 mmol) dropwise and the resulting mixture was stirred at rt for 15 h. Additional sulfuryl chloride (0.084 g, 0.62 mmol) was added and stirring was continued for 1 h. The mixture was partially concentrated to ˜½ volume under a stream of N2 and the resulting light yellow crystals were collected by filtration and washed sequentially with cold AcOH and hexanes, to afford the title compound (2.58 g, 74% yield): 1H NMR (400 MHz, CDCl3) δ 10.49 (s, 1H), 8.05 (d, J=9.3 Hz, 1H), 7.74 (d, J=7.6 Hz, 2H), 7.58-7.54 (m, 2H), 7.46-7.30 (m, 7H), 7.22 (d, J=9 Hz, 1H), 5.19 (s, 2H).
Workup
- stirringstirring
- waitwas continued for 1 h
- concentrationThe mixture was partially concentrated
- filtrationthe resulting light yellow crystals were collected by filtration
- washwashed sequentially with cold AcOH and hexanes
Sources & evidence
- ORD record
- ord-519f444ee23c4f04bfc94ad1c2a27448
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026262B2
Reaction notes
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