Pyrrolidine → HCID 59238965, compound

HRID 1949119Notes

Reaction equation

Br[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([F:15])[CH:12]=3)[NH:7][C:6]=2[C:5]([O:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[C:4]2[NH:22][C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][C:28]=3[C:3]=12.[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:4]1[C:5]([O:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[C:6]3[NH:7][C:8]4[CH:9]=[CH:10][C:11]([F:15])=[CH:12][C:13]=4[C:14]3=[C:2]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[C:3]2=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 2-(12-bromo-2,10-difluoro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)-N,N-dimethylethanamine (35.2 mg, 0.07681 mmol), pyrrolidine (19.1 μL, 0.2304 mmol), Pd(OAc)2 (5.2 mg, 0.02304 mmol), BINAP (14.3 mg, 0.02304 mmol) and sodium tert-butoxide (22.1 mg, 0.2304 mmol) in toluene (5 mL) was purged with high-purity Ar for five minutes and sealed with Teflon cap. The reaction tube was heated to 200° C. in a Smith Microwave Reactor for 10 minutes. The solvents were removed via vacuum pump. The residue was subjected to flash chromatography to provide the title compound (5.2 mg, 15%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.53 (s, 2 H), 7.70 (dd, J=10.0, 2.4 Hz, 2 H), 7.47 (dd, J=8.8, 4.8 Hz, 2 H), 7.19 (td, J=9.2, 2.4 Hz, 2 H), 4.29 (t, J=5.6 Hz, 2 H), 3.52-3.45 (m, 4 H), 2.72 (t, J=5.6 Hz, 2 H), 2.40-2.39 (m, 10 H); MS (ESI) m/z 447.2 (M−H)−; MS (ESI) m/z 449.0 (M+H)+

Workup

customwas purged with high-purity Ar for five minutes
customsealed with Teflon
customcap
customThe solvents were removed via vacuum pump

Sources & evidence

ORD record: ord-6dfc59bb0b4f4f63b60c2970cd010fe5
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399502B2

Reaction notes

Loading…