Triethylamine → 9-[4-(4-{[Tert-butyl(dimethyl)silyl]oxy}phenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 2035961Notes

Reaction equation

HRID 2035961 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:18]=[S:19]1(=[O:36])[CH2:24][CH2:23][N:22]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=3)[C:21]2=[N:20]1.C(N(CC)CC)C>CN(C=O)C.C(O[Cu]OC(=O)C)(=O)C>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:35][C:32]2[CH:31]=[CH:30][C:29]([C:28]3[C:21]4=[N:20][S:19](=[O:36])(=[O:18])[CH2:24][CH2:23][N:22]4[CH:25]=[CH:26][CH:27]=3)=[CH:34][CH:33]=2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 667478174-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

Product 1

HCID 667481279-[4-(4-{[Tert-butyl(dimethyl)silyl]oxy}phenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 46.7%

Reagents, catalysts & solvents 2

HCID 178476681HCID 178476681, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(tert-butyldimethylsilyloxy)phenylboronic acid (6.11 g), 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (2.23 g), triethylamine (5.61 mL), diacetoxycopper (2.93 g), and 4A MS (2.0 g) in DMF (80 mL) was stirred at room temperature overnight. The mixture was added with silica gel, concentrated in vacuo, and purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (1.82 g) as a white solid.

Workup

  1. additionThe mixture was added with silica gel
  2. concentrationconcentrated in vacuo
  3. custompurified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-a89481d055884a938e16e524ec489a14
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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