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Triethylamine → 6-[(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)amino]-2-chloro-5-fluoronicotinonitrile

HRID 603471
Notes
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Reaction equation

HRID 603471 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:9][C:10]1[N:17]=[C:16]([NH:18][CH2:19][CH2:20][CH2:21][OH:22])[C:15]([F:23])=[CH:14][C:11]=1[C:12]#[N:13].ClC1N=C(Cl)C(F)=CC=1C#N.CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Si:1]([O:22][CH2:21][CH2:20][CH2:19][NH:18][C:16]1[C:15]([F:23])=[CH:14][C:11]([C:12]#[N:13])=[C:10]([Cl:9])[N:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 866045982-Chloro-5-fluoro-6-[(3-hydroxypropyl)amino]nicotinonitrile

Product 1

HCID 866045976-[(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)amino]-2-chloro-5-fluoronicotinonitrileYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of t-butyldimethylsilyl chloride (0.73 g, 4.79 mmol) in CH2Cl2 (21 mL) was added 2-chloro-5-fluoro-6-[(3-hydroxypropyl)amino]nicotinonitrile [prepared as in Example 302] and starting from 2,6-dichloro-5-fluoronicotinonitrile] (1.0 g, 4.35 mmol), followed by Et3N (0.48 g, 4.79 mmol) and DMAP (0.01 g, 0.09 mmol). The resulting cloudy mixture was stirred at rt for 18 h, and then diluted with CH2Cl2. The organic layer was washed with water, dried (MgSO4), filtered, and then concentrated under reduced pressure. The product (1.47 g, 98%) was isolated after silica gel flash chromatography (2:1 hexanes/EtOAc) as a white solid. 1H NMR (400 MHz, CD3OD) δ 7.46 (d, 1H), 3.67 (t, 2H), 3.49 (t, 2H), 1.77 (qt, 2H), 0.84 (s, 9H), 0.00 (s, 6H).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7078c9a0e7cc4a53abfd760571e3d72c
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07906653B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes