Bromine → 2-bromo-4H,5H,6H,7H-thieno(2,3-c)pyridine hydrobromide

HRID 1888470Notes

Reaction equation

HRID 1888470 reaction equation
[Br:1]Br.Cl.[S:4]1[C:8]2[CH2:9][NH:10][CH2:11][CH2:12][C:7]=2[CH:6]=[CH:5]1>C(O)(=O)C>[BrH:1].[Br:1][C:5]1[S:4][C:8]2[CH2:9][NH:10][CH2:11][CH2:12][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 250673334,5,6,7-Tetrahydrothieno(2,3-c)pyridine--hydrogen chloride (1/1)

Product 1

HCID 670276802-bromo-4H,5H,6H,7H-thieno(2,3-c)pyridine hydrobromideYield 176.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (139 mg, 0.87 mmol) in acetic acid (0.5 mL) was added to a solution of 4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrochloride (150 mg, 0.85 mmol) in acetic acid (3 mL) and the mixture left to stir at ambient temperature for 1.5 h. The resultant precipitate was collected by filtration, washed with diethyl ether and left to air dry to afford the title compound as an off-white solid (230 mg, 90%). 1H NMR (DMSO-D6, 300 MHz): 9.19 (s, 2H), 7.09 (s, 1H), 4.29-4.26 (m, 2H), 2.86-2.78 (m, 2H), 2.52-2.48 (m, 2H). LCMS (Method B): RT=1.65 min, M+H+=218/220.

Workup

  1. waitthe mixture left
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with diethyl ether
  4. waitleft to air
  5. customdry

Sources & evidence

ORD record
ord-f8391308da5d472fa294631585fc4c47
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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