Boron tribromide → HCID 59425169, compound

HRID 252545Notes

Reaction equation

HRID 252545 reaction equation
[O:1]=[S:2]1(=[O:28])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH2:26][CH3:27])[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24]C)[CH:16]=3)=[CH:9][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[O:28]=[S:2]1(=[O:1])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]([CH2:26][CH3:27])[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([OH:24])[CH:16]=3)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11589308HCID 11589308, compound

Product 1

HCID 59425169HCID 59425169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure in example 1B step A, 2-[4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile is treated with 1M BBr3 solution in CH2Cl2 at −15° C. for 1.5 h and then poured into ice-water and filtered and dried to afford 2-[4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]-1-ethyl-6-hydroxy-1H-indole-3-carbonitrile in nearly quantitative yield.

Workup

  1. filtrationfiltered
  2. customdried

Sources & evidence

ORD record
ord-e19d60d5d4ee4bd6b95a5093f0a0042c
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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