Sodium Hydroxide → HCID 67228219, compound

HRID 1515768Notes

Reaction equation

HRID 1515768 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:20][CH:21]2[CH2:25][CH2:24][CH2:23][O:22]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C.O1CCCC1.ClCCl>[CH3:35][S:32]([C:29]1[CH:28]=[CH:27][C:26](/[C:19](/[C:11]2[NH:10][C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=2)=[CH:20]/[CH:21]2[CH2:25][CH2:24][CH2:23][O:22]2)=[CH:31][CH:30]=1)(=[O:33])=[O:34]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67229375HCID 67229375, compound

Product 1

HCID 67228219HCID 67228219, compoundYield 75.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-benzenesulfonyl-2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-furan-2-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (0.24 g, 0.47 mmol) in ethanol (2 mL), tetrahydrofuran (2 mL) and an aqueous sodium hydroxide solution (10%, 1 mL) was heated at 50° C. for 2 h. The mixture diluted with dichloromethane (50 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded (Z)-2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-furan-2-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (130 mg, 75%): LC/MS m/e calcd for C20H20N2O3S [M+H]+ 369.46, observed 369.3; and (E)-2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-furan-2-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (5 mg, 2%): LC/MS m/e calcd for C20H20N2O3S [M+H]+ 369.46, observed 369.3; 1H NMR (400 MHz, CD3OD) δ ppm 8.28 (d, J=5.1 Hz, 1H), 8.20 (d, J=7.8 Hz, 1H), 8.07-8.11 (m, J=8.3 Hz, 2H), 7.61-7.66 (m, J=8.1 Hz, 2H), 7.29-7.34 (m, 1H), 6.59 (d, J=9.1 Hz, 1H), 6.15 (s, 1H), 4.24 (q, J=7.4 Hz, 1H), 3.98 (q, J=7.0 Hz, 1H), 3.75-3.81 (m, 1H), 3.23 (s, 3H), 2.05-2.15 (m, 2H), 1.80-1.99 (m, 2H).

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification

Sources & evidence

ORD record
ord-a15f7278150049989aa00bda97aedb2c
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

Loading…