1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Bromo-6-fluorobenzo[b]thiophene

HRID 523573Notes

Reaction equation

HRID 523573 reaction equation
[Br:1][C:2]1[C:13]([F:14])=[CH:12][C:5]2[S:6][C:7](C(O)=O)=[CH:8][C:4]=2[CH:3]=1.C1CCN2C(=NCCC2)CC1>CC(N(C)C)=O>[Br:1][C:2]1[C:13]([F:14])=[CH:12][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 709830545-Bromo-6-fluorobenzo[b]thiophene-2-carboxylic acid

Product 1

HCID 709824575-Bromo-6-fluorobenzo[b]thiopheneYield 55%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Using analogous reaction condition and reagents as described in Example 25 for the preparation of I-25c above, 5-bromo-6-fluorobenzo[b]thiophene-2-carboxylic acid (I-28c: 240 mg 0.875 mmol) in DMA (4 mL) and DBU (0.523 mL, 3.503 mmol) were heated in microwave to afford the crude product. Purification by column chromatography on silica gel (100% hexane) afforded 110 mg of the product (55% yield).

Workup

  1. temperaturewere heated in microwave
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (100% hexane)

Sources & evidence

ORD record
ord-bf601e5492dc4559a66530bedd6a43c9
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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