Iodine → (R)-2-(6-chloro-5-iodo-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 418530Notes

Reaction equation

HRID 418530 reaction equation
N([O-])=O.[Na+].C[Si](C)(C)[Si](C)(C)C.[I:13]I.C(Cl)(Cl)(Cl)Cl.[C:20]([O:23][CH2:24][C@H:25]([N:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([Cl:38])[C:33]=2N)[C:28]1=[O:39])[CH3:26])(=[O:22])[CH3:21].C(Cl)Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:20]([O:23][CH2:24][C@H:25]([N:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([Cl:38])[C:33]=2[I:13])[C:28]1=[O:39])[CH3:26])(=[O:22])[CH3:21]

Participants

8

Reactant 6

HCID 807IodineHCID 5943Carbon TetrachlorideHCID 6344DichloromethaneHCID 74057HexamethyldisilaneHCID 23668193Sodium NitriteHCID 59515650(R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 59845699(R)-2-(6-chloro-5-iodo-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

To a solution of sodium nitrite (1 g, 0.02 mol), hexamethyldisilane (3 g, 0.02 mol), iodine (5 g, 0.02 mol) and benzyltriethylammonium chloride (0.3 g, 0.001 mol) in carbon tetrachloride (100 mL, 1 mol) was added a solution of (R)-2-(5-amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate (2.3 g, 0.0070 mol) in methylene chloride (3 mL, 0.05 mol) at 0° C. The mixture was stirred at the same temperature for 40 minutes and then warmed to room temperature overnight. The mixture was purified by flash chromatography to afford the desired product as a brown oil.

Workup

  1. customThe mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-29b42dbfbb3549c78406336b1ff3a430
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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