Sodium periodate → 2-(3-Phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazole-7-carbaldehyde

HRID 1506485Notes

Reaction equation

HRID 1506485 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]3[S:17][C:18]4[C:28]5[C:23](=[CH:24][C:25]([CH:29]([OH:32])CO)=[CH:26][CH:27]=5)[CH2:22][CH2:21][C:19]=4[N:20]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O>[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]3[S:17][C:18]4[C:28]5[C:23](=[CH:24][C:25]([CH:29]=[O:32])=[CH:26][CH:27]=5)[CH2:22][CH2:21][C:19]=4[N:20]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 671707831-(2-(3-Phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-yl)ethane-1,2-diol

Product 1

HCID 866699012-(3-Phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazole-7-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 1-(2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-yl)ethane-1,2-diol (Example 83, 0.233 g, 0.508 mmol) in THF (3 mL) was added sodium periodate (0.163 g, 0.762 mmol) in 2 mL of water over a period of 2 min. at room temperature and the contents stirred at room temperature for 30 min. The reaction mixture was partitioned between EtOAc (60 mL) and water (20 mL). The EtOAc layer was concentrated, the yellow solid that was obtained was azeotroped with acetonitrile (20 mL), dried under a high vacuum. Yield: (183 mgs, 83%); LC/MS M+1=427.

Workup

  1. customThe reaction mixture was partitioned between EtOAc (60 mL) and water (20 mL)
  2. concentrationThe EtOAc layer was concentrated
  3. customthe yellow solid that was obtained
  4. customwas azeotroped with acetonitrile (20 mL)
  5. customdried under a high vacuum

Sources & evidence

ORD record
ord-ed53d7b4ae804410ac83741263bfab9a
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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