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Sodium Iodide → 5-(2-chloro-4-cyanophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-5-carboxylic acid methyl ester

HRID 1877928
Notes
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Reaction equation

HRID 1877928 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][C:18]=1[Cl:25])[N:5]1[C:9]([CH2:10][CH2:11]OS(C)(=O)=O)=[CH:8][N:7]=[CH:6]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].CCN(CC)CC>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][C:18]=2[Cl:25])[N:5]2[CH:6]=[N:7][CH:8]=[C:9]2[CH2:10][CH2:11]1)=[O:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 86611069HCID 86611069, compound

Product 1

HCID 588270505-(2-chloro-4-cyanophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

The crude (2-chloro-4-cyanophenyl)-[5-(2-methanesulfonyloxyethyl)imidazol-1-yl]-acetic acid methyl ester (2.56 g, 6.45 mmol) is dissolved in dry DMF (50 mL) and to it is added K2CO3 (2.67 g, 19.4 mmol), NaI (2.9 g, 19.4 mmol) and Et3N (2.7 mL, 19.4 mmol). The reaction is stirred at 80° C. for 2 h before being concentrated to dryness. The residue is then diluted with EtOAc and washed with water. The organic layer is dried (Na2SO4) and evaporated to give a crude residue that is purified via flash column chromatography (Acetone/CH2Cl2 1:3) to give 5-(2-chloro-4-cyanophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-5-carboxylic acid methyl ester as an oil. MS (ESI) m/z 302.2, 304.2 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 2.64-2.76 (m, 2 H), 2.97-3.06 (m, 1 H), 3.84 (s, 3 H), 3.86-3.93 (m, 1 H), 6.56 (d, J=8.1 Hz, 1 H), 6.87 (s, 1 H), 7.50 (obs d, J=8.1 Hz, 1 H), 7.52 (s, 1 H), 7.73 (s, 1 H).

Workup

  1. concentrationbefore being concentrated to dryness
  2. additionThe residue is then diluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. customevaporated
  6. customto give a crude residue that
  7. customis purified via flash column chromatography (Acetone/CH2Cl2 1:3)

Sources & evidence

ORD record
ord-16503e18f07a4da6a19d5abc784e2bf6
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08314097B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes