Pyridine → HCID 21876712, compound

HRID 723787Notes

Reaction equation

HRID 723787 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[CH2:14][CH2:13][S:12][CH2:11][CH:10]=2)=[C:4]([F:15])[CH:3]=1.N1C=CC=CC=1.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>ClCCl>[CH2:26]([O:25][C:23]([NH:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[CH2:14][CH2:13][S:12][CH2:11][CH:10]=2)=[C:4]([F:15])[CH:3]=1)=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 21876582HCID 21876582, compound

Product 1

HCID 21876712HCID 21876712, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(4-Amino-2,6-difluorophenyl)-5,6-dihydro-2H-thiopyran (15.0 g, 66 mM) was dissolved in dry dichloromethane (250 ml), pyridine (9.45 g, 113 mM) added, and the whole stirred under nitrogen at −20°. Benzyl chloroformate (17.1 g, 100 mM) in dry dichloromethane (25 ml) was added dropwise, and the mixture allowed to warm to ambient over 18 hours. The mixture was washed with hydrochloric acid (1M, 2×200 ml), then brine (200 ml) and dried (magnesium sulfate). Evaporation to a small volume and dilution with isohexane gave the desired product as a white solid (22.5 g).

Workup

  1. temperatureto warm
  2. washThe mixture was washed with hydrochloric acid (1M, 2×200 ml)
  3. dry with materialbrine (200 ml) and dried (magnesium sulfate)
  4. customEvaporation to a small volume and dilution with isohexane

Sources & evidence

ORD record
ord-f2a168d2dbd54af38e3d5340812cfd30
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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