4-Toluenesulfonyl chloride → HCID 71061467, compound

HRID 875422Notes

Reaction equation

HRID 875422 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[N+:8]([O-])[CH:9]=[CH:10][C:5]=2[N:4]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH:3]=1.[CH3:22][C:23]([NH2:30])([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:24].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl.ClCCl>[Cl:1][C:2]1[C:6]2[C:7]([NH:30][C:23]([CH3:24])([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:22])=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH:3]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 61017tert-OctylamineHCID 86720634HCID 86720634, compound

Product 1

HCID 71061467HCID 71061467, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of benzyl 3-chloro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate 5-oxide (2.6 g, 8.53 mmol) in chloroform was treated dropwise with 2,4,4-trimethylpentan-2-amine (6.026 mL, 37.54 mmol) and stirred for about 15 minutes. The mixture was cooled to 0° C. followed by the portion wise addition of p-toluenesulphonyl chloride (3.578 g, 18.77 mmol). The reaction mixture was then stirred at room temperature for about 1 hour, diluted with dichloromethane and washed with saturated aq. sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under vacuum to get viscous oil. The crude product was purified by silica gel column chromatography using ethyl acetate and hexane (1%) to yield benzyl 3-chloro-4-[(2,4,4-trimethylpentan-2-yl)amino]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (610.8 mg, 43%) as a pale yellow solid.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for about 1 hour
  2. washwashed with saturated aq. sodium bicarbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto get viscous oil
  7. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6718bf8a12964693860a9941d2000e9d
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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