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

HRID 572410Notes

Reaction equation

HRID 572410 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-18436254e8694b07913027848131cf8c
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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