1,8-Diazabicyclo(5.4.0)undec-7-ene → Benzo[b]thiophene, 6-bromo-5-fluoro-

HRID 523568Notes

Reaction equation

HRID 523568 reaction equation
[Br:1][C:2]1[C:3]([F:14])=[CH:4][C:5]2[CH:9]=[C:8](C(O)=O)[S:7][C:6]=2[CH:13]=1.C1CCN2C(=NCCC2)CC1>CC(N(C)C)=O>[Br:1][C:2]1[C:3]([F:14])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:13]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 709820566-Bromo-5-fluorobenzo[b]thiophene-2-carboxylic acid

Product 1

HCID 70982589Benzo[b]thiophene, 6-bromo-5-fluoro-Yield 87.5%

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, 6-bromo-5-fluoro-benzo[b]thiophene-2-carboxylic acid (I-27c: 250 mg 0.89 mmol) in DMA (4 mL) and DBU (550 mL, 3.6 mmol) were heated in microwave to afford the crude product. Purification by column chromatography on silica gel (100% hexane) afforded 180 mg of the product (86% 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-b9209cf7efe74335a651ddbafdf23358
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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