Tributylstannane → 6-Bromoisoquinolin-3-Amine

HRID 2109755Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Br:12])=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH2:13])[N:3]=1.C([SnH](CCCC)CCCC)CCC>O1CCOCC1>[Br:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:2]=[N:3][C:4]([NH2:13])=[CH:5]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1,6-dibromoisoquinolin-3-amine (0.20 g, 0.66 mmol) and tributyltin hydride (0.19 mL, 0.73 mmol) in 6 mL of dioxane in a sealable tube was added palladium tetrakistriphenylphosphine (0.038 g, 0.033 mmol). The tube was sealed and heated to 100° C. in a Personal Chemistry microwave unit for 10 minutes. The mixture was then concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel (5% to 50% EtOAc/hexanes) affording 6-bromoisoquinolin-3-amine. 1H NMR (400 MHz, CD3OD) δ ppm 8.74 (s, 1H) 7.72 (s, 1H) 7.70 (d, J=8.80 Hz, 1H) 7.27 (dd, J=8.80, 1.76 Hz, 1H) 6.68 (s, 1H).

Workup

customThe tube was sealed
concentrationThe mixture was then concentrated under reduced pressure
customthe residue was purified by flash chromatography on silica gel (5% to 50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-e0a33de1c98246719e0c80c3c57489a8
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514566B2

Reaction notes

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