Hydrochloric Acid → HCID 67158570, compound

HRID 549049Notes

Reaction equation

HRID 549049 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[CH:13]=[C:12]3[C:19]2[N:27]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)[CH2:4][O:3]1.Cl>CO>[CH3:18][N:14]1[C:15]2[C:11](=[CH:10][C:9]([O:8][CH2:7][C@H:5]([OH:6])[CH2:4][OH:3])=[CH:17][CH:16]=2)[C:12]([C:19]2[N:27]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:29])=[O:30])[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)=[CH:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67158648HCID 67158648, compound

Product 1

HCID 67158570HCID 67158570, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[5-({R}-(−)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [1.04 g, Reference Example 23(b)] in methanol (20 mL) was treated with hydrochloric acid (20 mL, 1M) then heated under reflux for 3 hours. The reaction mixture was concentrated in vacuo and the residue subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (2:1, v/v) to give the title compound (380 mg) as a clear oil. TLC: RF=0.2 (pentane/ethyl acetate: 1/2). MS: 492 (MH+).

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionthe residue subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (2:1

Sources & evidence

ORD record
ord-53445f61362c45ea94fe2f5fc1f0e1ba
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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