Sodium Thiosulfate → HCID 57537599, compound

HRID 1693708Notes

Reaction equation

HRID 1693708 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([CH:18]=2)[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[CH:6][N:5]=[C:4]2[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:21][C:3]=12.[I:30]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCCl.O.ClCCl>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([CH:18]=2)[C:13]([N:15]([CH3:16])[CH3:17])=[O:14])=[CH:6][N:5]=[C:4]2[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:29])[CH3:28])[CH:20]=[C:21]([I:30])[C:3]=12

Participants

7

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 57537598HCID 57537598, compound

Product 1

HCID 57537599HCID 57537599, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.117 g (2.59 mmol) of 5-[4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide was dissolved in 19 ml of anhydrous 1,2-dichloroethane. 1.506 g (6.69 mmol) of N-iodosuccinimide was added and the mixture irradiated in a microwave reactor to 140° C. for 30 minutes. Saturated aqueous solution of sodium thiosulfate was added and the resulting mixture stirred at ambient temperature, then diluted with water and dichloromethane. The aqueous phase was separated and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of 10% v/v methanol in ethyl acetate and hexanes to afford 904.7 mg (62%, 1.625 mmol) of (5-[4-chloro-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide as a brown oil. 1H-NMR [500 MHz, d6-DMSO] d 8.75 (m, 1H), 8.69 (m, 1H), 8.39 (m, 1H), 8.12 (s, 1H), 8.02 (m, 1H), 5.64 (s, 2H), 3.54 (t, 2H), 3.02 (s, 3H), 3.00 (s, 3H), 0.84 (t, 2H), 0.09 (s, 9H); MS [MH+] m/z: 557.

Workup

  1. customthe mixture irradiated in a microwave reactor to 140° C. for 30 minutes
  2. customThe aqueous phase was separated
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customevaporated
  6. customThe resulting crude was purified by flash chromatography on silica gel using a gradient of 10% v/v methanol in ethyl acetate and hexanes

Sources & evidence

ORD record
ord-2ceb8cd1bd0b488ebacf98456bb46dfc
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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