Triethylamine → 3-Formyl-2-methyl-8-(2-(trans)-methylsulfonyloxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridine

HRID 1195743Notes

Reaction equation

HRID 1195743 reaction equation
C(N(CC)CC)C.[CH:8]([C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:18]([O:19][C@@H:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][C@H:21]3[OH:29])[C:13]2=[N:12][C:11]=1[CH3:30])=[O:9].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[CH:8]([C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:18]([O:19][C@@H:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][C@H:21]3[O:29][S:32]([CH3:31])(=[O:34])=[O:33])[C:13]2=[N:12][C:11]=1[CH3:30])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 228438253-Formyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine

Product 1

HCID 228438343-Formyl-2-methyl-8-(2-(trans)-methylsulfonyloxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8.5 ml triethylamine is added, while stirring and excluding any moisture, to 10 g 3-formyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine, suspended in 200 ml dry dichloromethane. This is cooled in an icebath and 5 ml methane sulfonyl chloride dissolved in 10 ml dry dichloromethane is added dropwise. This is stirred for 1 hour while cooling with ice, and the solution is poured onto icewater and extracted several times with dichloromethane. The organic phases are washed with water and dried, and the solvent is stripped off in vacuo. The yellowish residue is stirred with diethyl ether, filtered off under suction and dried. 12 g of the title compound of m.p. 158°-160° C. is obtained. By analogous methods 2-methyl-8-(2-(trans)methylsulfonyloxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridine is obtained from 2-methyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridine and methane sulfonyl chloride. M.p. 122°-125° C. (decomposition).

Workup

  1. additionis added dropwise
  2. stirringThis is stirred for 1 hour
  3. temperaturewhile cooling with ice
  4. additionthe solution is poured onto icewater
  5. extractionextracted several times with dichloromethane
  6. washThe organic phases are washed with water
  7. customdried
  8. stirringThe yellowish residue is stirred with diethyl ether
  9. filtrationfiltered off under suction
  10. customdried

Sources & evidence

ORD record
ord-cce343358ad24aa694f8333ac01fb7b1
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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