Potassium Phosphate, Tribasic → 2-Cyclopropyl-1-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-1h-indole

HRID 2264693Notes

Reaction equation

[CH:1]1([C:4]2[NH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:3][CH2:2]1.I[C:14]1[CH:28]=[CH:27][C:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:16][CH:15]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)CCN>C1(C)C=CC=CC=1.[Cu](I)I>[CH:1]1([C:4]2[N:5]([C:14]3[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:23][CH2:24][CH2:25][CH2:26]4)=[CH:27][CH:28]=3)[C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-cyclopropyl-1H-indole (17 mg, 0.11 mmol) and 1-[3-(4-iodophenoxy)propyl]pyrrolidine (36 mg. 0.11 mmol) in toluene (0.2 mL) was added copper iodide (0.2 mg), potassium phosphate (47 mg, 0.22 mmol), and N,N-dimethylethylenediamine (1.2 μL, 0.11 mmol). The reaction was stirred at 100° C. overnight. After cooling to room temperature, the reaction was filtered through a pad of silica. The reaction was concentrated and purified by preparative HPLC to give 1.6 mg of the desired indole. LC-MS (C24H28N2O calc'd 360) m/z 361 (M+H); 1H NMR (300 MHz, CDCl3) d 7.55-7.52 (m, 1H), 7.35-7.32 (m, 2H), 7.10-7.02 (m, 5H), 6.16 (s, 1H), 4.11 (t, J=6.3 Hz, 2H), 2.70 (t, J=7.5 Hz, 2H), 2.59 (m, 4H), 2.08 (quint, J=7.0 Hz, 1H), 1.83 (m, 2H), 1.64 (m, 4H), 0.88-0.81 (m, 2H), 0.79-0.73 (m, 2H).

Workup

temperatureAfter cooling to room temperature
filtrationthe reaction was filtered through a pad of silica
concentrationThe reaction was concentrated
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-be7bbcffa5cf4b2e9c0c2a5331ce1bd9
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855224B2

Reaction notes

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