Dichloromethane → HCID 71115359, compound

HRID 1502446Notes

Reaction equation

HRID 1502446 reaction equation
[F:1][C@H:2]1[CH2:4][C@H:3]1[C:5]([NH:7][C:8]1[N:9]=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18]1[CH:19]=[N:20][C:21]([CH:25]([OH:30])[C:26]([F:29])([F:28])[F:27])=[CH:22][C:23]=1[CH3:24])[CH:12]=2)=[O:6].ClCCl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:36]>S([O-])([O-])(=O)=S.[Na+].[Na+]>[F:1][C@H:2]1[CH2:4][C@H:3]1[C:5]([NH:7][C:8]1[N:9]=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18]1[CH:19]=[N:20][C:21]([C:25]([OH:36])([OH:30])[C:26]([F:29])([F:28])[F:27])=[CH:22][C:23]=1[CH3:24])[CH:12]=2)=[O:6]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 159087Triacetoxyperiodinane2×HCID 71115246HCID 71115246, compound

Product 1

HCID 71115359HCID 71115359, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 24477Sodium ThiosulfateSolvent

Procedure

A solution of (1S,2S)-2-fluoro-N-(7-(4-methyl-6-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-3-yl)isoquinolin-3-yl)cyclopropanecarboxamide (139.1 mg; 0.3317 mmol) in dichloromethane (5 mL; 78.00 mmol) was treated with Dess-Martin periodinane (172.7 mg; 0.3950 mmol) and stirred at room temperature. After 3 hours, additional Dess-Martin periodinane was added (142 mg). After an additional 5 hours, 30 mL of 10% aqueous sodium thiosulfate was added and the reaction mixture stirred for 10 minutes. The reaction mixture was washed with 2 M aqueous sodium carbonate, dried over MgSO4, filtered, and concentrated to yield 113.8 mg (79%) of the title compound. LCMS (ESI): M+H=436.2.

Workup

  1. waitAfter an additional 5 hours
  2. stirringthe reaction mixture stirred for 10 minutes
  3. washThe reaction mixture was washed with 2 M aqueous sodium carbonate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cc13e1477354420ab5432a98c8d7d480
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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