Tetrabutylammonium Fluoride → HCID 57936216, compound

HRID 1435023Notes

Reaction equation

HRID 1435023 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)[N:3]=1.C([Si](C)(C)[N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](B(O)O)=[CH:25]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]3[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]3)[N:3]=2)=[CH:25]1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 10989478{1-[tert-Butyl(dimethyl)silyl]-1H-indol-3-yl}boronic acidHCID 57936167(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

Product 1

HCID 57936216HCID 57936216, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

The title compound was prepared analogous to Step C of Method C, starting from (4-chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amine and [1-(tert-butyl-dimethyl-silanyl)-1H-indol-3-yl]-boronic acid using bis(triphenylphosphine)palladium(II) dichloride as a catalyst. The TBDMS protecting group was cleaved in situ by addition of catalytic amounts of TBAF. Yield: 2.2 g (86%).

Sources & evidence

ORD record
ord-610f8439e67b499fbc7400fbc8b785e5
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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