Triethylamine → 4-(2-((Tert-butyldimethylsilyloxy)methyl)pyridin-4-yloxy)-2-fluorobenzenamine

HRID 2042060Notes

Reaction equation

HRID 2042060 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][OH:14])[CH:8]=2)=[CH:4][C:3]=1[F:17].CCN(CC)CC.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>CN(C=O)C>[Si:25]([O:14][CH2:13][C:9]1[CH:8]=[C:7]([O:6][C:5]2[CH:15]=[CH:16][C:2]([NH2:1])=[C:3]([F:17])[CH:4]=2)[CH:12]=[CH:11][N:10]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 67253926HCID 67253926, compound

Product 1

HCID 672534314-(2-((Tert-butyldimethylsilyloxy)methyl)pyridin-4-yloxy)-2-fluorobenzenamineYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4-(4-amino-3-fluorophenoxy)pyridin-2-yl)methanol (750 mg, 3.2 mmol) and Et3N (821 mg, 8 mmol) in DMF (10 ml) at 0° C. was treated with tert-butyldimethylsilyl chloride (624 mg, 4.16 mmol). The resulting solution was stirred at RT for 4 hours. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography to provide 4-(2-((tert-butyldimethylsilyloxy)methyl)pyridin-4-yloxy)-2-fluorobenzenamine (370 mg, 33% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.32 (d, J=5.6 Hz, 1H), 7.02 (s, 1H), 6.67-6.82 (m, 4H), 4.76 (s, 2H), 3.71 (s, 2H), 0.89 (s, 9H), 0.07 (s, 6H); MS (ESI) m/z: 349.2 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f3aed3de57a94e6b9538cd0efd589f1a
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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