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

HRID 572415Notes

Reaction equation

HRID 572415 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-67bb2f9f1b934a73a297bc1324829b66
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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