Sodium Iodide → HCID 66607956, compound

HRID 563639Notes

Reaction equation

HRID 563639 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][N:25]([C:28](=[O:31])[CH2:29]Cl)[CH2:26][CH3:27])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC#N.CCOC(C)=O.O>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][N:25]([CH2:26][CH3:27])[C:28](=[O:31])[CH2:29][N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium Carbonate2×HCID 31268PyrrolidineHCID 66607317HCID 66607317, compound

Product 1

HCID 66607956HCID 66607956, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2′-{[(2-Chloro-acetyl)-ethyl-amino]-methyl}-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.55 mmol), pyrrolidine (0.05 mL, 0.61 mmol), potassium carbonate (0.152 g, 1.1 mmol), and sodium iodide (0.082 g, 0.55 mmol) were combined in MeCN (3 mL), and the reaction was stirred for 3 hours at room temperature. Analytical LCMS indicated that some starting material was still present, so additional potassium carbonate (0.053 g, 0.39 mmol) was added, and the reaction was stirred for 45 minutes. The mixture was diluted with EtOAc and H2O, and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried and concentrated to give the title compound.

Workup

  1. stirringthe reaction was stirred for 45 minutes
  2. extractionthe aqueous layer was extracted twice with EtOAc
  3. customThe combined organic layers were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-318e7f2883174af6b8bfa12e0b81910c
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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