Aluminium lithium hydride → 2-(5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)ethanol

HRID 931614Notes

Reaction equation

[N:1]([C:4]1([CH2:20][C:21](OC(C)(C)C)=[O:22])[C:17]2[C:12](=[N:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[O:11][C:10]2[C:5]1=[CH:6][C:7]([I:19])=[CH:8][CH:9]=2)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][C:4]1([CH2:20][CH2:21][OH:22])[C:17]2[C:12](=[N:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[O:11][C:10]2[C:5]1=[CH:6][C:7]([I:19])=[CH:8][CH:9]=2

Participants

Conditions

Temperature: 0 °C

Procedure

In a 1-L flask, the tert-butyl 2-(5-azido-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate (7.27 g, 13.38 mmol) was suspended in THF (100 mL) and the suspension was cooled to 0° C. A THF solution of LAH (1 M, 20.08 mL, 20.08 mmol) was added. After 30 min, the reaction mixture was quenched with careful addition of water (0.75 mL), 4 M aqueous NaOH (2.2 mL), and water (0.75 mL). The mixture was filtered through Celite, rinsing with THF (60 mL), then with EtOAc (150 mL). The combined filtrate was concentrated. The residue was purified through silica gel (400 mL) which had been deactivated with Et3N (40 mL), using 100:100:1 EtOAc-hexane-Et3N, to afford 2-(5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)ethanol (2.24 g).

Workup

customthe reaction mixture was quenched with careful addition of water (0.75 mL), 4 M aqueous NaOH (2.2 mL), and water (0.75 mL)
filtrationThe mixture was filtered through Celite
washrinsing with THF (60 mL)
concentrationThe combined filtrate was concentrated
customThe residue was purified through silica gel (400 mL) which

Sources & evidence

ORD record: ord-e6a4f565334949c4bf4de6dcb60784cc
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296759B2

Reaction notes

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