Diisopropylamine → HCID 70982345, compound

HRID 523558Notes

Reaction equation

HRID 523558 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:21])(=O)=O)=CC=1.C([Li])CCC.C(NC(C)C)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([F:21])[S:7][C:6]=2[CH:10]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 588007N-FluorobenzenesulfonimideHCID 127444006-Bromo-benzo[b]thiopheneHCID 178418339Butyllithium

Product 1

HCID 70982345HCID 70982345, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using analogous reaction condition and reagents as described Example 20 for the preparation of I-20a, 6-bromo-benzo[b]thiophene (I-25c: 0.5 g, 2.347 mmol) in dry THF was reacted with N-fluorobenzenesulfonimide (1.33 g, 4.22 mmol), n-butyl lithium (1.76 ml, 3.52 mmol), diisopropyl amine (0.57 ml, 3.99 mmol) to afford crude product. Purification by column chromatography on silica gel (100% hexane) afforded 176 mg of the product (33% yield).

Workup

  1. customto afford crude product
  2. customPurification by column chromatography on silica gel (100% hexane)

Sources & evidence

ORD record
ord-a8f371bc171e4029bed3587ce83cf9e5
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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