Triacetoxyperiodinane → 1-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)ethanone

HRID 588136Notes

Reaction equation

HRID 588136 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([OH:10])[CH3:9])[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.[OH-].[Na+]>[Cl:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[CH3:9])[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 1182717611-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)ethanol

Product 1

HCID 1182722641-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)ethanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

1-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)ethanol (38B, 130 mg, 0.277 mmol) was taken up in DCM (2.87 ml) and Dess-Martin periodinane (141 mg, 0.332 mmol) was added. The reaction was allowed to stir at rt for 1 hr. The reaction was diluted with DCM (8 ml) and 1N NaOH was added (15 ml) and the mixture was allowed to stir. The organic phase was separated and the aqueous was washed with DCM (20 ml×3). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo to give 1-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)ethanone (Intermediate 39B). The products were carried forward without purification. MS: [M+H]+ m/z 468.

Workup

  1. additionwas added (15 ml)
  2. stirringto stir
  3. customThe organic phase was separated
  4. washthe aqueous was washed with DCM (20 ml×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38074e12096a48b9a3f23f6b4e36485c
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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