Triacetoxyperiodinane → HCID 117840160, compound

HRID 1477728Notes

Reaction equation

HRID 1477728 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([OH:14])[CH2:12][N:11]([C:15]3[N:20]=[CH:19][N:18]([CH2:21][C:22]4[S:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=4)[C:17](=[O:31])[N:16]=3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13](=[O:14])[CH2:12][N:11]([C:15]3[N:20]=[CH:19][N:18]([CH2:21][C:22]4[S:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=4)[C:17](=[O:31])[N:16]=3)[CH2:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 159087Triacetoxyperiodinane2×HCID 516892Sodium BicarbonateHCID 78166221HCID 78166221, compound

Product 1

HCID 117840160HCID 117840160, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-[4-(4-fluorophenyl)-5-hydroxy-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (20.0 mg, 0.0442 mmol) synthesized in Synthesis Example 190, dichloromethane (1.0 mL), sodium bicarbonate (11.1 mg, 0.132 mmol), and Dess-Martin periodinane (28.1 mg, 0.0663 mmol; manufactured by Tokyo Chemical Industry Co., Ltd.) were added and the resultant mixture was stirred at room temperature for 1 day. Then, to the reaction solution, dichloromethane (4.0 mL) and Dess-Martin periodinane (30.0 mg, 0.0707 mmol) were added and the resultant mixture was stirred at room temperature for 2 hours. After the completion of the reaction, the reaction solution was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (19.4 mg, yield: 98%).

Workup

  1. additionwere added
  2. customAfter the completion of the reaction
  3. customthe reaction solution was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-d925b1aabc7a4fd18f08d903d353f33c
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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