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CAS No. : | 67004-64-2 | MDL No. : | MFCD00003174 |
Formula : | C7H15NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FYVMBPXFPFAECB-UHFFFAOYSA-N |
M.W : | 129.20 | Pubchem ID : | 93363 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2% | In a 24-well Bohdan block, ethyl 5-hydroxy-1 /-/-indole-2-carboxylate (0.100 g, 0.487 mmol), 2-(1-methyl-2-pyrrolidinyl)ethanol (0.157 g, 1.22 mmol) and PS- triphenylphosphine (406 mg, 1.22 mmol) were dissolved in THF (1 ml_). Di-terf-butyl azodicarboxylate (1.22 M in THF, 1 ml.) was added and the block shaken overnight. The reactor block was drained into a second Bohdan block and rinsed with THF. 1 N LiOH (1 ml.) was added and the reactor block shaken for 6 hours at RT. 1 N HCI (1 ml.) was added and the block was drained into a 24-well plate, rinsed with THF and the solvent evaporated. The residue was dissolved in DMF and filtered to remove salts. To the DMF solution was added 3-[3-(aminomethyl)-6-chloro-2- fluorophenyl]oxy}-5-chlorobenzonitrile (50 mg, 0.161 mmol) followed by HATU (61.1 mg, 0.161 mmol) and DIPEA (30 mul_, 0.222 mmol) and the reaction mixture stirred overnight. The resulting solution was diluted to 2 ml. with MeOH. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.007 g, 2%) as a glass. 1H NMR (400 MHz, CDCI3)/ delta ppm 9.50 (br. s., 1 H), 7.22 - 7.39 (m, 4 H), 7.13 - 7.18 (m, 1 H), 7.05 - 7.12 (m, 1 H), 6.95 - 7.03 (m, 2 H), 6.84 - 6.91 (m, 2 H), 4.66 - 4.75 (m, 2 H), 4.07 - 4.17 (m, 1 H), 3.91 - 4.00 (m, 1 H), 3.27 - 3.41 (m, 1 H), 2.76 - 2.91 (m, 4 H), 2.39 - 2.51 (m, 1 H), 2.24 - 2.36 (m, 1 H), 2.16 (br. s., 2 H), 1.91 - 2.08 (m, 3 H). LCMS m/z 581.1 (M+1 ). |
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