Sodium Iodide → HCID 68283041, compound

HRID 1527258Notes

Reaction equation

HRID 1527258 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=2)[C:10]([Br:20])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+].[I-].[Na+]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:18])[CH:15]=2)[C:10]([Br:20])=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 68283540HCID 68283540, compound

Product 1

HCID 68283041HCID 68283041, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution containing 3-bromo-indazole-1,6-dicarboxylic acid 1-tert-butyl ester (1.80 g, 5.28 mmol), benzylbromide (0.753 mL, 6.33 mmol), Cs2CO3 (1.89 g, 5.80 mmol) and sodium iodide (0.095 g, 0.633 mmol) in DMF (30 mL) was stirred 16 h at RT. The mixture was diluted with water and extracted with EtOAc (×3). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (EtOAc/c-hexane 1:4). MS (UPLC/MS): 431.2/433.2 [M+H]+; tR (UPLC conditions f): 2.77 min.

Workup

  1. extractionextracted with EtOAc (×3)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (EtOAc/c-hexane 1:4)
  6. custom2.77 min.

Sources & evidence

ORD record
ord-bad094883048460d8aa6e74172d8c133
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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