N-Iodosuccinimide → HCID 58118705, compound

HRID 1038982Notes

Reaction equation

HRID 1038982 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C@:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.[I:20]N1C(=O)CCC1=O>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][C:19]=1[I:20])[CH2:16][C@:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 53260812(R)-5-Amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2×

Product 1

HCID 58118705HCID 58118705, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (4.00 g, 15.9 mmol, described in Intermediate 1) in THF (64 mL) at ambient temperature was added N-iodosuccinimide (3.58 g, 15.92 mmol). The reaction mixture was stirred for 18 h, then purified by silica gel chromatography, eluting with EtOAc:hexanes—70:30, to give the title compound. MS: m/z=378 (M+1).

Workup

  1. custompurified by silica gel chromatography
  2. washeluting with EtOAc

Sources & evidence

ORD record
ord-7209e44719584f2c951524f7e08f9ae0
Source dataset
uspto-grants-2013_10
Patent number
US08552023B2

Reaction notes

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