Tetrabutylammonium Fluoride → HCID 57936342, compound

HRID 1435027Notes

Reaction equation

HRID 1435027 reaction equation
C([Si](C)(C)[N:6]1[C:14]2[CH:13]=[C:12]3[O:15][CH2:16][O:17][C:11]3=[CH:10][C:9]=2[CH:8]=[CH:7]1)(C)(C)C.Cl[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH:28]2[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][C:30]([CH3:37])([CH3:36])[CH2:29]2)[N:22]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[O:17]1[C:11]2=[CH:10][C:9]3[C:8]([C:25]4[CH:26]=[CH:21][N:22]=[C:23]([NH:27][CH:28]5[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][C:30]([CH3:37])([CH3:36])[CH2:29]5)[N:24]=4)=[CH:7][NH:6][C:14]=3[CH:13]=[C:12]2[O:15][CH2:16]1

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 57936167(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amineHCID 69063856HCID 69063856, compound

Product 1

HCID 57936342HCID 57936342, compound

Procedure

The title compound was prepared as described in Example 215, starting from 5-(tert-butyl-dimethyl-silanyl)-5H-[1,3]dioxolo[4,5-f]indole (prepared by TBDMS protection of 5H-[1,3]Dioxolo[4,5-f]indole) and (4-chloro-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine, followed by in situ cleavage of the TBDMS protecting group with catalytic amounts of TBAF. Yield: 555 mg (87%).

Sources & evidence

ORD record
ord-f5f56d541f8b4cb8805fe5def0b3a3aa
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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