Ethanol → HCID 178469171, compound

HRID 1912612Notes

Reaction equation

HRID 1912612 reaction equation
[F:1][C:2]1[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][CH2:7]/[C:6]/1=[N:10]\[C:11](=[C:13]([C:19](OCC)=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:12].[O-]CC.[Na+].CCO.Cl.O>CN(C)C=O>[F:1][C:2]1[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:6]2=[N:10][C:11]([CH3:12])=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]([OH:20])=[C:7]2[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 21885828Hydrate;hydrochloride2×HCID 178472264HCID 178472264, compound

Product 1

HCID 178469171HCID 178469171, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-diethyl 2-(1-((1-(2,3-difluorobenzyl)pyrrolidin-2-ylidene)amino)ethylidene)malonate (36.3 g, 69.9 mmol) in N,N-dimethylformamide (DMF) (140 mL) was added sodium ethoxide (78 mL, 210 mmol) (21% wt./EtOH) and the mixture was placed in a pre-heated oil bath at 100° C. and stirred for 1 h. The mixture was cooled to ambient temperature and then poured slowly into cold 1 N HCl/water (−150 mL) and then more 1N HCl/water was added to pH 8-9. After stirring at 0° C. for 30 min The solid was filtered, washed with water and dried in vacuo for 18 h to provide ethyl 1-(2,3-difluorobenzyl)-4-hydroxy-6-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (10 g, 27.3 mmol, 39.0% yield) as a light tan solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.42 (t, J=7.12 Hz, 3 H), 2.66 (s, 3 H), 2.95 (t, J=8.68 Hz, 2 H), 3.53 (t, J=8.78 Hz, 2 H), 4.39 (q, J=7.02 Hz, 2 H), 4.72 (s, 2 H), 6.90-7.20 (m, 3 H), 11.94 (s, 1 H); LCMS (m/z) ES+=349 (M+1).

Workup

  1. customthe mixture was placed in a pre-heated oil bath at 100° C.
  2. stirringAfter stirring at 0° C. for 30 min The solid
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried in vacuo for 18 h

Sources & evidence

ORD record
ord-865b0c87707d4b108377df999fa7d187
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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