Methanol → HCID 178526243, compound

HRID 2192145Notes

Reaction equation

HRID 2192145 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[NH:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=[CH:13]1.CO>ClCCl>[NH:12]1[C:16]2=[N+:17]([O-:9])[CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=[CH:13]1

Participants

5

Reactant 3

HCID 887MethanolHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 178526243HCID 178526243, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(Antonini, Ippolito; Claudi, Francesco; Cristalli, Gloria; Franchetti, Palmarisa; Grifantini, Mario; Martelli, Sante; J. Med. Chem. 1982, 25(10), 1258-1261) 540 g (2.35 mol) of 3-chloroperbenzoic acid are dissolved in 6.11 l of dichloromethane, and the water that separates off is removed. The organic phase is dried over sodium sulfate and cooled to 0° C. A solution of 163 g (1.38 mol) of 1H-pyrrolo[2,3-b]pyridine (Hands, D.; Bishop, B.; Cameron, M.; Edwards, T. S.; Cottrell, I. F.; Wright, S. H. B.; Synthesis 1996 (7), 877-882) in 1.00 l of dichloromethane is then added, and the temperature is allowed to rise to room temperature. After 2 hours, such an amount of methanol is added that the precipitate formed redissolves. The mixture is filtered through silica gel (mobile phase: dichloromethane/methanol 95:5). After concentration, the product fractions are dried under high vacuum.

Workup

  1. customthe water that separates off is removed
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customto rise to room temperature
  4. customformed
  5. dissolutionredissolves
  6. filtrationThe mixture is filtered through silica gel (mobile phase: dichloromethane/methanol 95:5)
  7. concentrationAfter concentration
  8. customthe product fractions are dried under high vacuum

Sources & evidence

ORD record
ord-b2e2a765bc8a4c49b85f4b6f409afe56
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

Loading…