Methanol → HCID 178526243, compound

HRID 2240208Notes

Reaction equation

HRID 2240208 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, 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, 877-882.) in 1.00 l of dichloromethane is then added, and the temperature is allowed to rise to room temperature. After 2 hours, methanol is added in such an amount that the precipitate formed redissolves. The mixture is filtered through silica gel (mobile phase:dichloromethane/methanol 95:5) and the product fractions are, after concentration, 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. customdried under high vacuum

Sources & evidence

ORD record
ord-1a8999604a5548a8ad9e206e7aea512b
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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