Dimethyl Sulfoxide → (R)-2-(5-Iodo-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 1625004Notes

Reaction equation

N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@H:13]([CH3:19])[CH2:14][O:15][C:16](=[O:18])[CH3:17])[C:7]2=[O:12].N([O-])=O.[Na+].CS(C)=O.[IH:28].C([O-])([O-])=O.[Na+].[Na+]>>[I:28][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@H:13]([CH3:19])[CH2:14][O:15][C:16](=[O:18])[CH3:17])[C:7]2=[O:12]

Participants

Reactant 5

HCID 679Dimethyl Sulfoxide2×

HCID 10340Sodium Carbonate

HCID 24841Hydrogen iodide

HCID 23668193Sodium Nitrite

HCID 59515825(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 67203267(R)-2-(5-Iodo-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Procedure

Acetic acid (R)-2-(5-amino-1-oxo-1H-isoquinolin-2-yl)-propyl ester (790 mg, 0.0030 mol) was added to a solution of sodium nitrite (800 mg, 0.01 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) at room temperature. Aqueous hydrogen iodide (4 mL, 0.03 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) was added. The reaction mixture was stirred at room temperature for 1 hour. The cooled reaction mixture was neutralized with saturated aq. Na2CO3 and extracted with methylene chloride (3×100 mL). The combined methylene chloride extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was chromatographed on 40 of silica gel column (0-50% EtOAc/Hexane) to give the desired product as a brown oil. MS m/z (M+H) 371.9

Workup

customThe cooled reaction mixture
extractionextracted with methylene chloride (3×100 mL)
washThe combined methylene chloride extracts were washed with brine
dry with materialdried over magnesium sulfate
customThe solvent was removed in vacuo
customthe residue was chromatographed on 40 of silica gel column (0-50% EtOAc/Hexane)

Sources & evidence

ORD record: ord-1882d9c5f9fc480ba716ff280449d7bc
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779144B2

Reaction notes

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