Ethyl 4-aminocyclohexanecarboxylate → 4-[4-(4-Bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid ethyl ester

HRID 1516441Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:11]1[CH:16]=[CH:15][N:14]=[C:13](S(C)=O)[N:12]=1.[CH2:20]([O:22][C:23]([CH:25]1[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]1)=[O:24])[CH3:21]>O1CCOCC1>[CH2:20]([O:22][C:23]([CH:25]1[CH2:30][CH2:29][CH:28]([NH:31][C:13]2[N:12]=[C:11]([N:6]3[C:7]4[C:3](=[C:2]([Br:1])[CH:10]=[CH:9][CH:8]=4)[CH:4]=[CH:5]3)[CH:16]=[CH:15][N:14]=2)[CH2:27][CH2:26]1)=[O:24])[CH3:21]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 4-bromo-1-(2-methylsulfinyl-pyrimidin-4-yl)-1H-indole (4.98 g) and 4-amino-cyclohexanecarboxylic acid ethyl ester (5.07 g) in 1,4-dioxane (100 mL) was stirred at 110° C. under N2 for 5.5 h. The solvent was removed in vacuo to provide an oil, which solidified at RT. The product was flash chromatographed on silica, eluting with hexanes/EtOAc (7:3 to 6:4) to provide 4-[4-(4-bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid ethyl ester (5.82 g, 89%) as a white powder.

Workup

customThe solvent was removed in vacuo
customto provide an oil, which
customsolidified at RT
customchromatographed on silica
washeluting with hexanes/EtOAc (7:3 to 6:4)

Sources & evidence

ORD record: ord-39c24d042ab24c2e8b9f85214ab3a62a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227478B2

Reaction notes

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