Hydrochloric Acid → 6-fluoro-3-iodo-1H-indole-5-carboxylic acid

HRID 634299Notes

Reaction equation

HRID 634299 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].[I:14]I.[OH-].[K+].S([O-])(O)=O.[Na+].Cl>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:14])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]([OH:13])=[O:12]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 14797Potassium HydroxideHCID 114920336-fluoro-1H-indole-5-carboxylic acidHCID 23665763Sodium Bisulfite

Product 1

HCID 683284516-fluoro-3-iodo-1H-indole-5-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-fluoro-1H-indole-5-carboxylic acid (2.32 g, 12.95 mmol) in DMF (15 mL) was added iodine (3.45 g, 13.60 mmol) and potassium hydroxide (1.60 g, 28.5 mmol). After stirring 20 min at RT, the reaction mixture was poured into ice water (40 mL) containing sodium hydrogensulfite (1.35 g, 12.95 mmol). The reaction mixture was stirred for 5 min, treated with 2 N HCl to adjust the pH to about pH=6 and filtered. The resulting orange solid was washed with water (2×25 mL) and transferred to a 250 mL round bottomed flask and dried overnight using a lyophilizer to afford 6-fluoro-3-iodo-1H-indole-5-carboxylic acid (3.63 g, 11.90 mmol, 92% yield) as an orange amorphous solid. MS (ESI, pos. ion) m/z: 305.9 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for 5 min
  2. filtrationfiltered
  3. washThe resulting orange solid was washed with water (2×25 mL)
  4. customtransferred to a 250 mL round bottomed flask
  5. customdried overnight

Sources & evidence

ORD record
ord-dc92b6bc798e429c83e97dd62e7ae7fd
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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