Triacetoxyperiodinane → HCID 178440925, compound

HRID 1640174Notes

Reaction equation

HRID 1640174 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][C:18]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]([C:31]5[NH:32][CH:33]=[C:34]([CH2:36][OH:37])[N:35]=5)[CH:26]=4)=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][C:18]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]([C:31]5[NH:32][CH:33]=[C:34]([CH:36]=[O:37])[N:35]=5)[CH:26]=4)=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 18470521Sodium bicarbonate sodium sulfiteHCID 178440926HCID 178440926, compound

Product 1

HCID 178440925HCID 178440925, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-(3-tert-butylphenyl)-7-({2-[4-(hydroxymethyl)-1H-imidazol-2-yl]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxamide (I-3) (1.24 g, 2.50 mmol) in DCM (10 mL) was added Dess-Martin periodinane (1.27 g, 3.00 mmol) at rt. The resulting suspension was allowed to stir at rt for 30 min, and then aqueous NaHCO3/Na2SO3 solution (1:1) was added and the mixture was extracted with DCM (30 mL×3). The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated to give N-(3-tert-butylphenyl)-7-{[2-(4-formyl-1H-imidazol-2-yl)pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalene-2-carboxamide as a yellow foam which was used without further purification. LCMS: (FA) ES+ 495.5.

Workup

  1. extractionthe mixture was extracted with DCM (30 mL×3)
  2. washThe combined organic solutions were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-96533c6067254cea8727ae09044733e4
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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