HCID 94920062, compound → HCID 76328420, compound

HRID 925117Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]2([C:17]#[N:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:5]([N+:19]([O-])=O)[CH:4]=1.[H][H]>CC(O)=O.[Pd]>[CH3:10][O:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[N:19]=[C:17]([NH2:18])[C:11]12[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

Conditions

Temperature: 70 °C

Procedure

1-(4,5-Dimethoxy-2-nitrophenyl)cyclohexanecarbonitrile (0.251 g, 0.865 mmol), prepared in Step 2, in AcOH (6 mL) was treated with 10% Pd/C, fitted with hydrogen balloon and heated to 70° C. for 3 hours under hydrogen atmosphere. The catalyst was filtered off and washed with EtOH. The solvent was concentrated. Purification by reverse phase HPLC afforded 17 mg (8%) of 5′,6′-dimethoxyspiro[cyclohexane-1,3′-indol]-2′-amine 1H NMR (400 MHz, DMSO) δ 7.11 (s, 1H), 6.64 (s, 1H), 3.72 (s, 3H), 3.70 (s, 3H), 1.88-1.84 (m 4H), 1.82-1.66 (m, 4H), 1.22 (d, J=10.2 Hz, 2H). MS (ESI) m/z 261 (M+H)+.

Workup

filtrationThe catalyst was filtered off
washwashed with EtOH
concentrationThe solvent was concentrated
customPurification by reverse phase HPLC

Sources & evidence

ORD record: ord-75d9ab6bacec4723a1635636f821fbd6
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284272B2

Reaction notes

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