Reserpine → HCID 68680671, compound

HRID 645665Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.CO[C@@H]1[C@@H](C(OC)=O)[C@@H:23]2[C@@H:14]([CH2:15][N:16]3[C@H:21]([CH2:22]2)C2NC4C=C(OC)C=CC=4C=2CC3)[CH2:13][C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O.C(#[N:55])C>>[F:1][C:2]1[N:3]=[CH:4][C:5]([O:8][C:15]2[N:16]=[CH:21][CH:22]=[CH:23][C:14]=2[C:13]#[N:55])=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 5770Reserpine

HCID 6342Acetonitrile2×

HCID 27631086-Fluoropyridin-3-ol

Product 1

HCID 68680671HCID 68680671, compound

Procedure

The title compound was synthesized according to General Procedure 9 using 2-fluoro-5-hydroxypyridine. 1H NMR (DMSO-d6, 400 MHz) δ 7.33 (dd, 1H, J=3.3 Hz, J=8.8 Hz), 7.37 (dd, 1H, J=5.0 Hz, J=7.6 Hz), 8.01 (ddd, 1H, J=3.0 Hz, J=6.7 Hz, J=8.9 Hz), 8.26 (dd, 1H, J=1.6 Hz, J=2.9 Hz), 8.40 (dd, 1H, J=1.9 Hz, J=5.0 Hz), 8.47 (dd, 1H, J=1.9 Hz, J=7.6 Hz); RP-HPLC (Hypersil®-100 C18, 5 μm, 100 Å, 10 cm; 5%-100% acetonitrile-0.1M ammonium acetate over 5 min. 2 mL/min), then 100% acetonitrile isocratic 1 minutes, Rt 3.67 min.

Sources & evidence

ORD record: ord-4a6656028d68496c966a0f99d0066956
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07704997B1

Reaction notes

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