Indole → (4-Indol-1-yl-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

HRID 1435020Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)[N:3]=1.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1.[OH-].[K+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(OC(=O)C)C>[N:19]1([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]3[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]3)[N:3]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (4-chloro-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (200 mg, 0.74 mmol), indole (96 μl, 0.81 mmol), potassium hydroxide (63 mg, 1.10 mmol) and a few drops of Aliquat 336 were heated to 120° C. for 5 h. After cooling to room temperature the mixture was dissolved in ethylacetate, washed with water and brine and the crude product was purified by HPLC. Thus 71 mg (0.20 mmol, 27%) of the title compound were obtained.

Workup

temperatureAfter cooling to room temperature the mixture
washwashed with water and brine
customthe crude product was purified by HPLC

Sources & evidence

ORD record: ord-789f7a5a5cef4542933d3b9e9b1c990d
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615562B2

Reaction notes

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