Tetrabutylammonium Fluoride → HCID 57936350, compound

HRID 1435036Notes

Reaction equation

HRID 1435036 reaction equation
C([Si](C)(C)[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[Cl:15])[CH:8]=[CH:7]1)(C)(C)C.Cl[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH:25][CH:26]2[CH2:31][C:30]([CH3:33])([CH3:32])[NH:29][C:28]([CH3:35])([CH3:34])[CH2:27]2)[N:20]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[Cl:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[NH:6][CH:7]=[C:8]2[C:23]1[CH:24]=[CH:19][N:20]=[C:21]([NH:25][CH:26]2[CH2:31][C:30]([CH3:33])([CH3:32])[NH:29][C:28]([CH3:35])([CH3:34])[CH2:27]2)[N:22]=1

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 57936167(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amineHCID 69067435HCID 69067435, compound

Product 1

HCID 57936350HCID 57936350, compound

Procedure

The title compound was prepared as described in Example 215, starting from 1-(tert-butyl-dimethyl-silanyl)-7-chloro-1H-indole (prepared by TBDMS protection of 7-chloro-1H-indole 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: 280 mg (34%).

Sources & evidence

ORD record
ord-a2401639aedf40978fe6fae0627dba6f
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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