Hydrogen iodide → HCID 66712774, compound

HRID 1406152Notes

Reaction equation

[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Br)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].I>>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 24841Hydrogen iodide

HCID 86595473HCID 86595473, compound

Product 1

HCID 66712774HCID 66712774, compoundYield 34%

Procedure

540 mg of 1-bromo-4-hydroxy-6-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (1.25 mmol) were reacted with red phosphorous and HI analogously to Example D-1 f). The crude product was purified by flash column chromatography on silica gel eluting with hexanes:ethyl acetate (85:15). 150 mg of the title compound were obtained; 1H NMR (CDCl3): δ=11.78 (s, 1 H), 8.71 (d, 1 H), 8.11 (t, 1 H), 7.79 (d, 1 H), 7.39 to 7.54 (m, 6 H), 4.49 (t, 2 H), 1.87 (m, 2 H), 1.47 (m, 2 H), 0.98 (t, 3 H).

Workup

customThe crude product was purified by flash column chromatography on silica gel eluting with hexanes:ethyl acetate (85:15)

Sources & evidence

ORD record: ord-969764e3a7f845b39c350987bcaf3804
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916585B2

Reaction notes

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