Bromine → 3-Bromo-4-fluorothieno[2,3-c]pyridine

HRID 389541Notes

Reaction equation

HRID 389541 reaction equation
[F:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][CH:9]=[CH:10][C:3]=12.C([O-])(=O)C.[Na+].[Br:16]Br>C(O)(=O)C>[Br:16][C:10]1[C:3]2[C:4](=[CH:5][N:6]=[CH:7][C:2]=2[F:1])[S:8][CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 667606654-Fluorothieno[2,3-c]pyridine

Product 1

HCID 667610953-Bromo-4-fluorothieno[2,3-c]pyridineYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-fluorothieno[2,3-c]pyridine (100 mg, 0.653 mmol) and sodium acetate (109 mg, 1.30 mmol) in acetic acid (2.65 mL) was added bromine (101 uL, 1.96 mmol). The reaction was heated in a microwave at 90° C. for 90 min. The reaction was concentrated. Purification by ISCO chromatography (5 to 40% ethyl acetate:heptane) afforded 77 mg (51%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.96 (s, 1 H), 8.40 (d, J=2.3 Hz, 1 H), 7.67 (d, J=0.8 Hz, 1 H); MS (ESI): 231.99, 233.95 [M+H]+; HPLC tR=3.28 min (ZQ3, polar—4 min).

Workup

  1. concentrationThe reaction was concentrated
  2. customPurification by ISCO chromatography (5 to 40% ethyl acetate:heptane)

Sources & evidence

ORD record
ord-e0caecd841e94720ba6b211c8948113f
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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