Hydrazine → 6-fluoro-3-iodo-1-tosyl-1H-indole-5-carbohydrazide

HRID 634301Notes

Reaction equation

HRID 634301 reaction equation
C1C=CC2N(O)[N:8]=[N:7]C=2C=1.CCN=C=NCCCN(C)C.Cl.[F:23][C:24]1[CH:32]=[C:31]2[C:27]([C:28]([I:43])=[CH:29][N:30]2[S:33]([C:36]2[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=2)(=[O:35])=[O:34])=[CH:26][C:25]=1[C:44]([OH:46])=O.NN>O.CN(C=O)C>[F:23][C:24]1[CH:32]=[C:31]2[C:27]([C:28]([I:43])=[CH:29][N:30]2[S:33]([C:36]2[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=2)(=[O:35])=[O:34])=[CH:26][C:25]=1[C:44]([NH:7][NH2:8])=[O:46]

Participants

7

Reactant 4

HCID 9321HydrazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 683283216-fluoro-3-iodo-1-tosyl-1H-indole-5-carboxylic acid

Product 1

HCID 683288316-fluoro-3-iodo-1-tosyl-1H-indole-5-carbohydrazideYield 245.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HOBt (Aldrich, St. Louis, Mo., 303 mg, 2.24 mmol), EDC HCl (430 mg, 2.242 mmol) and 6-fluoro-3-iodo-1-tosyl-1H-indole-5-carboxylic acid (858 mg, 1.87 mmol) were weighed into a 250 mL round bottomed flask and treated with DMF (7 mL). The resulting solution was stirred at RT for 30 min. The reaction mixture was then treated with anhydrous hydrazine (0.29 mL, 9.34 mmol) and stirred at RT for 30 min. The reaction mixture was diluted with water resulting in precipitate formation. The solid was collected by filtration, washed with water, and dried under high vacuum for 3 h at 50° C., affording crude 6-fluoro-3-iodo-1-tosyl-1H-indole-5-carbohydrazide (2.17 g) as a light yellow amorphous solid. MS (ESI, pos. ion) m/z: 473.9 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.59 (1H, br. s.), 8.17 (1H, s), 8.01 (2H, d, J=8.4 Hz), 7.97 (5H, s), 7.82 (1H, d, J=10.8 Hz), 7.50 (1H, d, J=6.5 Hz), 7.45 (3H, d, J=8.2 Hz), 4.56 (2H, br. s.), 4.11 (3H, br. s.), 2.36 (4H, s).

Workup

  1. stirringstirred at RT for 30 min
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried under high vacuum for 3 h at 50° C.

Sources & evidence

ORD record
ord-3c360c7675da4ce29fd55ac2a84afc1a
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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