Diisopropylethylamine → HCID 90019210, compound

HRID 2175058Notes

Reaction equation

HRID 2175058 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C@H:8]2[NH2:11])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[C:24]([Cl:31])[N:23]=1>>[Cl:31][C:24]1[N:23]=[C:22]([NH:11][C@H:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=3)[CH2:6][CH2:7]2)[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 40466991(1R)-6-Fluoro-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 90019210HCID 90019210, compoundYield 100.2%

Procedure

Purge a 12 L 3-necked flask with nitrogen, and then assemble thermocouple, heating mantle and condenser. Charge (1R)-6-fluoro-2,3-dihydro-1H-inden-1-amine (386 g, 2.55 mol) to the flask, add 3A-EtOH (3.9 L), diisopropylethylamine (1.34 L, 7.68 mol), and 2,6-dichloro-3-nitropyridine (643 g, 3.07 moles). Stir the reaction mixture at ambient temperature for eight hours followed by heating to 70° C. for 12 hours. Cool the reaction mixture to 8° C. over 1.25 h, then filter onto a polypropylene pad. Wash the solids with 3A-EtOH (760 mL), transfer to a tared dish and further dry in a vacuum oven (45° C.) to afford the title compound as an orange solid (786 g, 71%, 98.0% ee). GC/MS (m/z): 307 (M+).

Workup

  1. customPurge a 12 L 3-necked flask with nitrogen
  2. temperatureheating mantle and condenser
  3. temperatureby heating to 70° C. for 12 hours
  4. temperatureCool the reaction mixture to 8° C. over 1.25 h
  5. filtrationfilter onto a polypropylene pad
  6. washWash the solids with 3A-EtOH (760 mL), transfer to a tared dish
  7. customfurther dry in a vacuum oven (45° C.)

Sources & evidence

ORD record
ord-ee020f1bd14d4b09bc696fb3d7b83144
Source dataset
uspto-grants-2015_06
Patent number
US09062050B2

Reaction notes

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