Tetrabutylammonium Fluoride → HCID 57936289, compound

HRID 1435038Notes

Reaction equation

HRID 1435038 reaction equation
C([Si](C)(C)[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=2)[CH:8]=[CH:7]1)(C)(C)C.Cl[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH:29]2[CH2:34][C:33]([CH3:36])([CH3:35])[NH:32][C:31]([CH3:38])([CH3:37])[CH2:30]2)[N:23]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH3:35][C:33]1([CH3:36])[CH2:34][CH:29]([NH:28][C:24]2[N:23]=[C:22]([C:8]3[C:9]4[C:14](=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=4)[NH:6][CH:7]=3)[CH:27]=[CH:26][N:25]=2)[CH2:30][C:31]([CH3:38])([CH3:37])[NH:32]1

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 57936167(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amineHCID 69064856HCID 69064856, compound

Product 1

HCID 57936289HCID 57936289, compound

Procedure

The title compound was prepared as described in Example 215, starting from 1-(tert-butyl-dimethyl-silanyl)-6-trifluoromethyl-1H-indole (prepared by TBDMS protection of 6-trifluoromethyl-1H-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: 640 mg (77%).

Sources & evidence

ORD record
ord-7aa0b3f821854e03a35b2c156f0d9d16
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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