Diisopropylamine → HCID 70982008, compound

HRID 523553Notes

Reaction equation

HRID 523553 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6][CH:7]=[C:8]([CH3:9])[C:4]=2[CH:3]=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:22])(=O)=O)=CC=1.C(NC(C)C)(C)C.C([Li])CCC>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6][C:7]([F:22])=[C:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 588007N-FluorobenzenesulfonimideHCID 141757645-Bromo-3-methyl-1-benzothiopheneHCID 178418339Butyllithium

Product 1

HCID 70982008HCID 70982008, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using analogous reaction condition and workup as described in Example 20 above from the preparation of I-20a, 5-bromo-3-methyl-benzo[b]thiophene (I-24b: 500 mg, 2.192 mmol) in dry THF was reacted with N-fluoro benzene sulfonimide (1.2 g, 3.94 mmol), diisopropyl amine (266.2 mg, 2.6315 mmol), n-butyl lithium (1.3 mL, 2.6315 mmol) to afford crude product. Purification by column chromatography on silica gel (hexane) afforded 120 mg of the product (22% yield).

Workup

  1. customto afford crude product
  2. customPurification by column chromatography on silica gel (hexane)

Sources & evidence

ORD record
ord-2d7ccb81f6664e7fbe0a19200e469630
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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