1-Bromopropane → 5-Methoxy-2-phenyl-1-propyl-1H-indole

HRID 576582Notes

Reaction equation

Br[CH2:2][CH2:3][CH3:4].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:10]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:2][CH2:3][CH3:4])[C:11]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:10]2

Participants

Conditions

Temperature: 25 °C

Procedure

1-Bromopropane (0.248 g, 2.015 mmol) was added to a solution of 95A (0.15 g, 0.672 mmol) in DMF (5 mL) followed by cesium carbonate (0.657 g, 2.015 mmol), and the mixture was stirred at 25° C. for 12 h. Insoluble solids were filtered off, and filtrate was concentrated. Residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using 3% ethyl acetate in hexane as eluent to afford title compound (0.1 g, 56.1%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 7.54-7.5 (m, 4H), 7.46-7.39 (m, 2H), 7.06 (d, J=2.0 Hz, 1H), 6.8 (dd, J1=2.4 Hz, J2=8.8 Hz, 1H), 6.42 (s, 1H), 4.12 (t, J=7.2 Hz, 2H), 3.76 (s, 3H), 1.54 (m, 2H), 0.63 (t, J=7.2 Hz).

Workup

filtrationInsoluble solids were filtered off
concentrationfiltrate was concentrated
customResidue was partitioned between ethyl acetate and water
customOrganic layer was separated
washwashed with brine
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-64ea5d9b2e5446daab8d0c56b41b5ac1
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040517B2

Reaction notes

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