Water → HCID 86673615, compound

HRID 1023465Notes

Reaction equation

HRID 1023465 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)=[CH:12][CH:11]=1.C(N(CC)CC)C.O>CS(C)=O>[Cl:8][C:4]1[CH:3]=[C:2]([N:17]2[CH2:18][CH2:19][CH2:20][CH:16]2[C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 38477704-Bromo-2-chloropyridineHCID 38655602-(4-Fluorophenyl)pyrrolidine

Product 1

HCID 86673615HCID 86673615, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
200 °C

Procedure

4-Bromo-2-chloro-pyridine (0.17 mL, 1.5 mmol), 2-(4-fluoro-phenyl)-pyrrolidine (250 mg, 1.5 mmol) and triethylamine (0.22 mL, 1.6 mmol) are mixed in DMSO (5.0 mL). The reaction mixture is heated at 120° C. for 30 min and 200° C. for 40 min in a microwave reactor. Then water (35 mL) is added and the mixture is extracted with EtOAc (3×30 mL). The organic layers are combined, washed with water (3×20 mL) and concentrated to give the crude product. Purification by silica flash column chromatography using EtOAc in heptane (gradient from 10% to 90%) followed by Gilson preparative HPLC affords 240 mg of desired product.

Workup

  1. extractionthe mixture is extracted with EtOAc (3×30 mL)
  2. washwashed with water (3×20 mL)
  3. concentrationconcentrated
  4. customto give the crude product
  5. customPurification by silica flash column chromatography

Sources & evidence

ORD record
ord-40fd944b24854e6b922bd3f7a25ae573
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

Loading…