4-Toluenesulfonyl chloride → 5-fluoro-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde

HRID 1968255Notes

Reaction equation

HRID 1968255 reaction equation
[F:1][C:2]1[CH:7]=[N:6][C:5]2[NH:8][CH:9]=[C:10]([I:11])[C:4]=2[C:3]=1[CH:12]=[O:13].[OH-].[Na+].[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([S:23]([C:20]3[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=3)(=[O:25])=[O:24])[CH:9]=[C:10]([I:11])[C:4]=2[C:3]=1[CH:12]=[O:13]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 866542075-fluoro-3-iodo-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde

Product 1

HCID 582934925-fluoro-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4-carbaldehydeYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-fluoro-3-iodo-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde in DMF (12 mL) was added NaOH (0.716 g, 17.91 mmol). The deep red solution was stirred for 30 min after which 4-methylbenzene-1-sulfonyl chloride (3.13 g, 16.42 mmol) was added. The reaction mixture was stirred for 2 h, subsequently diluted with EtOAc, and washed with water and brine. The extracts were dried over MgSO4 and concentrated. Purification by silica column chromatography (DCM, 100%) afforded the title compound as light yellow solid (3.65 g, 55%). 1H NMR (400 MHz, DMSO-d6) δ 2.36 (s, 3 H) 7.45 (m, J=8.08 Hz, 2 H) 8.02 (m, J=8.34 Hz, 2H) 8.42 (s, 1 H) 8.59 (d, J=2.53 Hz, 1 H) 11.13 (s, 1 H). [M+H] calc'd for C15H10FIN2O3S, 445; found, 445.1.

Workup

  1. additionwas added
  2. washwashed with water and brine
  3. dry with materialThe extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customPurification by silica column chromatography (DCM, 100%)

Sources & evidence

ORD record
ord-0a9fd8f89bc946b2bc905ef40183b878
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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