Sodium Thiosulfate → 7-Chloro-3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 2264927Notes

Reaction equation

HRID 2264927 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[C:12]([Cl:15])=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Si](C)(C)C)=[CH:19][C:18]=1[F:27])=[O:5])[CH3:2].[I:28]Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[C:12]([Cl:15])=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([I:28])=[CH:19][C:18]=1[F:27])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24477Sodium Thiosulfate2×HCID 24640Iodine chlorideHCID 595965967-Chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 595966027-Chloro-3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl esterYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (0.91 g, 2.25 mmol) in dichloromethane (20 ml) at −10° C. was added iodine monochloride (4.95 ml, 4.95 mmol, 1M solution in dichloromethane) and the resultant mixture was stirred at −10° C. to 0° C. for 2 h. A saturated solution of sodium thiosulfate (25 ml) was added and the mixture was poured into saturated sodium thiosulfate (40 ml). The aqueous layer was extracted with ethyl acetate (3×35 ml) and the combined organic layers were washed with brine, dried over magnesium sulfate and concentrated in vacuo. The resultant residue was triturated in dichloromethane:cyclohexane 1:4 to afford the title compound as a yellow solid (0.87 g, 84%). LCMS (method B): RT=3.17 min, M+H+=460.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (3×35 ml)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was triturated in dichloromethane:cyclohexane 1:4

Sources & evidence

ORD record
ord-4b6de5a2964d4cb0becf5d764a6fbd7c
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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