Triethylamine → HCID 67469488, compound

HRID 630411Notes

Reaction equation

HRID 630411 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][OH:10])=[C:4]([O:11][CH3:12])[CH:3]=1.CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[C:29]([Si:33](Cl)([CH3:35])[CH3:34])([CH3:32])([CH3:31])[CH3:30]>O1CCCC1>[Si:33]([O:10][CH2:9][C:5]1[C:4]([O:11][CH3:12])=[CH:3][C:2]([NH2:1])=[C:7]([F:8])[CH:6]=1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 67469376HCID 67469376, compound2×

Product 1

HCID 67469488HCID 67469488, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4-amino-5-fluoro-2-methoxyphenyl)methanol (intermediate 91; 1.49 g, 8.7 mmol) in tetrahydrofuran (117 mL) was added dimethylaminopiridine (0.1 g, 0.81 mmol) and triethylamine (3.4 mL, 24.3 mmol). Then the mixture was cooled to 0° C. and tert-butylchlorodimethylsilane (2.45 g, 16.2 mmol) was added under argon atmosphere. The mixture was stirred 2 hours at room temperature. The solvent was removed under reduced pressure and the crude obtained was purified by column chromatography with silica gel, eluting with hexane/ether (from 0% to 100%). The title compound was obtained as an pale-orange solid (82%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude obtained
  3. customwas purified by column chromatography with silica gel
  4. washeluting with hexane/ether (from 0% to 100%)

Sources & evidence

ORD record
ord-59827b9c4e6b4b21a90216431994bd38
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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