Reserpine → HCID 68582993, compound

HRID 2240458Notes

Reaction equation

[CH2:1]([N:8]1[CH:12]=[C:11](B2OC(C)(C)C(C)(C)O2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C@@H]1[C@@H](C(OC)=O)[C@@H:36]2[C@@H:27]([CH2:28][N:29]3[C@H:34]([CH2:35]2)C2NC4C=C(OC)C=CC=4C=2CC3)[CH2:26][C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O.C(#[N:68])C>>[CH2:1]([N:8]1[CH:12]=[C:11]([C:28]2[N:29]=[CH:34][CH:35]=[CH:36][C:27]=2[C:26]#[N:68])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 5770Reserpine

HCID 6342Acetonitrile2×

HCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 68582993HCID 68582993, compound

Procedure

The title compound was prepared from 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole using General Procedure 3. 1H NMR (DMSO-d6, 400 MHz) δ 5.46 (s, 2H), 7.30-7.38 (m, 5H), 7.41 (dd, J=4.9 Hz, J=7.9 Hz, 1H), 8.21 (s, 1H), 8.30 (dd, J=1.8 Hz, J=7.9 Hz, 1H), 8.62 (s, 1H), 8.80 (dd, J=1.7 Hz, J=4.8 Hz, 1H); RP-HPLC (Hypersil® HS C18, 5 μm, 100 Å, 25 cm; 50%-100% acetonitrile-0.1M ammonium acetate over 10 min, 1 mL/min), then 100% acetonitrile isocratic 2 minutes, Rt 5.95 min. (99.0%), MS: M+H+ 261.

Sources & evidence

ORD record: ord-6cc265e0f9cd4cf1b11e351253ed23dd
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723367B2

Reaction notes

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