Sodium Iodide → HCID 59543146, compound

HRID 1971001Notes

Reaction equation

HRID 1971001 reaction equation
[CH:1]1([C@@H:4]([NH:9][C:10]2[C:22]3[C:21]4[CH:20]=[CH:19][C:18](B5OC(C)(C)C(C)(C)O5)=[CH:17][C:16]=4[NH:15][C:14]=3[C:13]([C:32]([NH2:34])=[O:33])=[CH:12][N:11]=2)[C:5]([F:8])([F:7])[F:6])[CH2:3][CH2:2]1.CC1C=CC(S([N-]Cl)(=O)=O)=CC=1.O.O.O.[Na+].[I-:51].[Na+]>C1COCC1.O.CCOC(C)=O>[CH:1]1([C@@H:4]([NH:9][C:10]2[C:22]3[C:21]4[CH:20]=[CH:19][C:18]([I:51])=[CH:17][C:16]=4[NH:15][C:14]=3[C:13]([C:32]([NH2:34])=[O:33])=[CH:12][N:11]=2)[C:5]([F:8])([F:7])[F:6])[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 5238Sodium IodideHCID 517414chloramine-T trihydrateHCID 59543138HCID 59543138, compound

Product 1

HCID 59543146HCID 59543146, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-pyrido[4,3-b]indole-4-carboxamide (0.17 g, 0.35 mmol) in THF (0.88 mL) and water (0.88 mL) were added chloramine T trihydrate (0.11 g, 0.39 mmol) and sodium iodide (0.079 g, 0.53 mmol). The reaction mixture was left to stir at room temperature for 2 h, diluted with EtOAc, and washed with water and brine. The organic layer was dried (sodium sulfate), concentrated, and purified by prep-HPLC to afford the title compound.

Workup

  1. waitThe reaction mixture was left
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated
  5. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-359dcf5cfd7944158472bb876dca13c3
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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