Sodium sulfate decahydrate → 2-(5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)ethanol

HRID 455619Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]([C:10]1([CH2:26][C:27](OCC)=[O:28])[C:23]2[C:18](=[N:19][CH:20]=[C:21]([Br:24])[CH:22]=2)[O:17][C:16]2[C:11]1=[CH:12][C:13]([I:25])=[CH:14][CH:15]=2)=[N+]=[N-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH2:7][C:10]1([CH2:26][CH2:27][OH:28])[C:23]2[C:18](=[N:19][CH:20]=[C:21]([Br:24])[CH:22]=2)[O:17][C:16]2[C:11]1=[CH:12][C:13]([I:25])=[CH:14][CH:15]=2

Participants

Conditions

Temperature: -78 °C

Procedure

LAH (1M in THF; 6.12 ml, 6.12 mmol) was added slowly to a −78 C cooled solution of ethyl 2-(5-azido-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate (2.10 g, 4.08 mmol) in THF (40.8 ml). The reaction mixture was stirred at −78° C. for 15 min, and the reaction mixture was allowed to warm to RT and stirred for additional 30 min. The reaction mixture was cooled to 0° C., quenched with sodium sulfate decahydrate (2.90 g, 20.38 mmol) and allowed to stir 20 min. The solution was filtered through a pad of celite, the filter cake was eluted with 10% MeOH/DCM and the filtrate was concentrated. The residue was purified via flash chromatography (0-25% EtOAc/CH2Cl2) to afford 2-(5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)ethanol as a yellow solid.

Workup

temperatureto warm to RT
stirringstirred for additional 30 min
temperatureThe reaction mixture was cooled to 0° C.
stirringto stir 20 min
filtrationThe solution was filtered through a pad of celite
washthe filter cake was eluted with 10% MeOH/DCM
concentrationthe filtrate was concentrated
customThe residue was purified via flash chromatography (0-25% EtOAc/CH2Cl2)

Sources & evidence

ORD record: ord-b7042d44be97428d995730f3c8eaa9d4
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497264B2

Reaction notes

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