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Sodium Iodide → (S)-tert-butyl 5-((3-fluoropyrrolidin-1-yl)methyl)pyridin-2-ylcarbamate

HRID 520497
Notes
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Reaction equation

HRID 520497 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1.[F:17][C@H:18]1[CH2:22][CH2:21][NH:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C>[F:17][C@H:18]1[CH2:22][CH2:21][N:20]([CH2:2][C:3]2[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=2)[CH2:19]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 7016277(S)-3-fluoropyrrolidineHCID 67993136Tert-butyl (5-chloromethylpyridin-2-yl)carbamate

Product 1

HCID 67993091(S)-tert-butyl 5-((3-fluoropyrrolidin-1-yl)methyl)pyridin-2-ylcarbamateYield 61%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of tert-butyl 5-(chloromethyl)pyridin-2-ylcarbamate 117(9.5 g, 39.1 mmol), (S)-3-fluoropyrrolidine 118 (4.19 g, 47.0 mmol), potassium carbonate (16.2 g, 117 mmol) and sodium iodide (0.586 g, 3.91 mmol) in DMF (150 mL) was stirred at 60° C. for 2 h. The reaction mixture was filtered, and the filtrate was concentrated in vacuo. H2O (250 mL) was added and the resulting solid was collected by filtration, rinsed with H2O and dried to give 119 (7.00 g, 61% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionH2O (250 mL) was added
  4. filtrationthe resulting solid was collected by filtration
  5. washrinsed with H2O
  6. customdried

Sources & evidence

ORD record
ord-1f6e0445f1c94379b5054b101ebbfe4e
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09326986B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes