Aluminium lithium hydride → HCID 67253926, compound

HRID 2042059Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[CH:27]=[CH:26][C:11]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19](OC(C)(C)C)=[O:20])[CH:14]=2)=[CH:10][C:9]=1[F:28]>C1COCC1>[NH2:7][C:8]1[CH:27]=[CH:26][C:11]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH2:19][OH:20])[CH:14]=2)=[CH:10][C:9]=1[F:28]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of LiAlH4 (699 mg, 18.4 mmol) in THF (15 mL) was added tert-butyl 4-(4-amino-3-fluorophenoxy)picolinate (1.4 g, 4.6 mmol) at 0° C. under N2. The mixture was stirred at 0° C. for 2 h. The reaction mixture was quenched with 10% aq NaOH solution (4 mL), the resultant suspension was filtered and the filtrate was extracted with EtOAc (3×30 mL) to give (4-(4-amino-3-fluorophenoxy)pyridin-2-yl)methanol (700 mg, 70% yield). MS (ESI) m/z: 235.1 (M+H+).

Workup

customThe reaction mixture was quenched with 10% aq NaOH solution (4 mL)
filtrationthe resultant suspension was filtered
extractionthe filtrate was extracted with EtOAc (3×30 mL)

Sources & evidence

ORD record: ord-64a1f3fcdd494978bba7e4fa60e0baba
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586565B2

Reaction notes

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