Potassium Fluoride → tert-butyl N-[4-(3-cyano-1-cyclobutyl-6-cyclopropyl-indol-2-yl)phenyl]carbamate

HRID 1009670Notes

Reaction equation

[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([CH:26]3[CH2:29][CH2:28][CH2:27]3)[C:16]3[C:21]([C:22]=2[C:23]#[N:24])=[CH:20][CH:19]=[C:18](Br)[CH:17]=3)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH:31]1(B(O)O)[CH2:33][CH2:32]1.[F-].[K+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([CH:26]3[CH2:29][CH2:28][CH2:27]3)[C:16]3[C:21]([C:22]=2[C:23]#[N:24])=[CH:20][CH:19]=[C:18]([CH:31]2[CH2:33][CH2:32]2)[CH:17]=3)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of [4-(6-bromo-3-cyano-1-cyclobutyl-1H-indol-2-yl)-phenyl]-carbamic acid tert-butyl ester (0.17 g, 0.4 mmol), cyclopropylboronic acid (0.047 g, 0.55 mmol), (tert-butyl)3PHBF4 (0.014 g, 0.048 mmol), KF (0.093 g, 1.6 mmol), and Pd2(dba)3-CHCl3, 0.021 g, 0.02 mmol) in THF (2.0 mL) was stirred at 60° C. overnight. The mixture was concentrated, taken up in CH2Cl2 and filtered through Celite. The solid was washed with CH2Cl2 and the filtrate was purified on silica gel (CH2Cl2) to provide [4-(3-cyano-1-cyclobutyl-6-cyclopropyl-1H-indol-2-yl)-phenyl]-carbamic acid tert-butyl ester as a solid (0.10 g, 59%).

Workup

concentrationThe mixture was concentrated
filtrationfiltered through Celite
washThe solid was washed with CH2Cl2
customthe filtrate was purified on silica gel (CH2Cl2)

Sources & evidence

ORD record: ord-5b01492a76df4a3185997435a50fefa9
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973069B2

Reaction notes

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