Tetrabutylammonium Fluoride → 3-[2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-1H-indole-7-carbonitrile

HRID 1435044Notes

Reaction equation

HRID 1435044 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]#[N:11])[CH:3]=[CH:2]1.Cl[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH:20]2[CH2:25][C:24]([CH3:27])([CH3:26])[NH:23][C:22]([CH3:29])([CH3:28])[CH2:21]2)[N:14]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH3:26][C:24]1([CH3:27])[CH2:25][CH:20]([NH:19][C:15]2[N:14]=[C:13]([C:3]3[C:4]4[C:9](=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[CH:18]=[CH:17][N:16]=2)[CH2:21][C:22]([CH3:29])([CH3:28])[NH:23]1

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 108988161H-Indole-7-carbonitrileHCID 57936167(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

Product 1

HCID 579363013-[2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-1H-indole-7-carbonitrile

Procedure

The title compound was prepared as described in Example 215, starting from SEM-protected 1H-indole-7-carbonitrile and (4-chloro-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine, followed by cleavage of the SEM-protecting group with TBAF. Yield: 10 mg (6%).

Sources & evidence

ORD record
ord-82135456a7b54f21858b70bf689b5ffc
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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