Triethylamine → HCID 10270024, compound

HRID 433134Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:14]2)(=O)=O)=CC=1.[F:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH:28]=[C:27]2[C:33]1[CH2:34][CH2:35][NH:36][CH2:37][CH:38]=1.C(N(CC)CC)C>C(OCC)(=O)C>[O:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:21][CH2:22][CH:13]1[CH2:12][N:36]1[CH2:37][CH:38]=[C:33]([C:27]2[C:26]3[C:30](=[CH:31][CH:32]=[C:24]([F:23])[CH:25]=3)[NH:29][CH:28]=2)[CH2:34][CH2:35]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3,4-dihydro-2H-chromen-2-ylmethyl 4-methylbenzenesulfonate (0.500 g, 1.57 mmol) was added 5-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.590 g, 2.73 mmol) and triethylamine (0.314 g, 3.10 mmol) and the reaction mixture was heated to 80° C. for 8 h. The reaction mixture was allowed to cool to room temperature and was diluted with ethyl acetate (200 mL), washed with water (3×100 mL), aqueous sodium chloride (100 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, methanol:dichloromethane 1:9) provided 0.234 g (40%) of 3-[1-(3,4-dihydro-2H-chromen-2-ylmethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-5-fluoro-1H-indole as a yellow solid. mp 172-175° C.; Anal. Calcd. for C23H23FN2O: C, 76.22; H, 6.40; N, 7.73. Found: C, 75.82; H, 6.37; N, 7.63.

Workup

temperatureto cool to room temperature
washwashed with water (3×100 mL), aqueous sodium chloride (100 mL)
dry with materialdried (magnesium sulfate)
customthe solvent was removed in vacuo
customto give a crude solid
customPurification by flash column chromatography (silica, methanol:dichloromethane 1:9)

Sources & evidence

ORD record: ord-59338705a45140d6a899ede40d2e1774
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06667322B2

Reaction notes

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