Bromine → 3-Thiocyano-2-methylpyrrolo[2,3-b]pyridine

HRID 1756105Notes

Reaction equation

HRID 1756105 reaction equation
[CH3:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.[S-:11][C:12]#[N:13].[Na+].BrBr>C(O)(=O)C>[S:11]([C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:10][C:2]=1[CH3:1])[C:12]#[N:13]

Participants

5

Reactant 3

HCID 24408BromineHCID 516871Sodium thiocyanateHCID 5830662-Methyl-7-azaindole

Product 1

HCID 193925873-Thiocyano-2-methylpyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of 300 mg (2.36 mmol) of 2-methylpyrrolo[2,3-b]pyridine and 920 mg (11.3 mmol) of sodium thiocyanate in 5 ml acetic acid was added 450 mg (2.8 mmol) bromine in 1 ml acetic acid at 5° C. The reaction mixture was stirred for 30 min at 5° C. and thereafter for 16 h at room temperature. The solid was filtered off. To the filtrate was added 20 ml water. The precipitated product was filtered off and washed with water giving 160 mg (37%) of the title compound.

Workup

  1. waitfor 16 h at room temperature
  2. filtrationThe solid was filtered off
  3. additionTo the filtrate was added 20 ml water
  4. filtrationThe precipitated product was filtered off
  5. washwashed with water giving 160 mg (37%) of the title compound

Sources & evidence

ORD record
ord-133db31bffce410abe5fb59799fb97e0
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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