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

HRID 634192Notes

Reaction equation

HRID 634192 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>CN(C=O)C.O>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[N:4]([S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 509905183-iodo-1H-indole-5-carboxylic acid

Product 1

HCID 683285993-iodo-1-tosyl-1H-indole-5-carboxylic acidYield 100.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-iodo-1H-indole-5-carboxylic acid (3.70 g, 12.89 mmol) in DMF (9.5 mL) at 0° C. was treated with NaH (60% in mineral oil) (1.289 g, 32.2 mmol). After 15 min at 0° C., p-toluenesulfonyl chloride (2.95 g, 15.47 mmol) was added in 1 g portions at 0° C. every 15 min and the reaction was warmed slowly in the ice bath to 10° C. After 2 h, the mixture was dumped into H2O and the mixture was acidified with 5 M HCl. The precipitate was collected by filtration, washed with water and dried to afford crude 3-iodo-1-tosyl-1H-indole-5-carboxylic acid (5.72 g) as a tan solid. MS (ESI, pos. ion) m/z: 442 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.20 (1H, s), 8.03-8.09 (1H, m), 7.93-8.02 (3H, m), 7.91 (1H, s), 7.42 (2H, d, J=8.0 Hz), 2.33 (3H, s)

Workup

  1. waitAfter 2 h
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-f87234bbc5474711bc6af55804f1f5fc
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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