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

HRID 418530노트

반응식

HRID 418530 반응식
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]

참가 물질

8

반응물 6

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

생성물 1

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

시약·촉매·용매 1

HCID 66133Benzyl triethylammonium chloride촉매

실험 절차

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.

후처리

  1. customThe mixture was purified by flash chromatography

출처 및 근거

ORD 기록
ord-29b42dbfbb3549c78406336b1ff3a430
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093265B2

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