Tetrabutylammonium Fluoride → HCID 69058730, compound

HRID 1435025Notes

Reaction equation

C([Si](C)(C)[N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)(C)(C)C.Cl[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH:27]2[CH2:32][C:31]([CH3:34])([CH3:33])[NH:30][C:29]([CH3:36])([CH3:35])[CH2:28]2)[N:21]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH3:33][C:31]1([CH3:34])[CH2:32][CH:27]([NH:26][C:22]2[N:21]=[C:20]([N:6]3[C:14]4[C:9](=[CH:10][C:11]([C:15]#[N:16])=[CH:12][CH:13]=4)[CH:8]=[CH:7]3)[CH:25]=[CH:24][N:23]=2)[CH2:28][C:29]([CH3:36])([CH3:35])[NH:30]1

Participants

Reactant 3

HCID 2724141Tetrabutylammonium Fluoride

HCID 57936167(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

HCID 69058586HCID 69058586, compound

Product 1

HCID 69058730HCID 69058730, compound

Procedure

The title compound was prepared as described in Example 215, starting from 1-(tert-butyl-dimethyl-silanyl)-1H-indole-5-carbonitrile (prepared by TBDMS protection of 1H-indole-5-carbonitrile using standard procedures) 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: 441 mg (26%)

Sources & evidence

ORD record: ord-e97c66d02c1d441d8a660001d6a40f3d
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615562B2

Reaction notes

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