2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-(2-(benzyloxy)ethyl)-2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole

HRID 1776855Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[N:16]2[C:17]3[CH:18]=[CH:19][CH:20]=[C:21]([F:24])[C:22]=3[CH2:23][CH:15]2[C:14]2[N:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:13]=2[O:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[N:16]2[C:17]3[CH:18]=[CH:19][CH:20]=[C:21]([F:24])[C:22]=3[CH:23]=[C:15]2[C:14]2[N:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:13]=2[O:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-(2-(benzyloxy)ethyl)-2-chloro-11-fluoro-12,12a-dihydro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (500 mg, 1.22 mmol) in toluene (7 mL) was added DDQ (552 mg, 2.43 mmol). The mixture was stirred at 80° C. for 2 hours. Then it was concentrated in vacuo, the resulting residue was purified using prep-HPLC to provide 6-(2-(benzyloxy)ethyl)-2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (44 mg, yield: 9%). 1H-NMR (CDCl3, 400 MHz) δ 7.32˜7.43 (m, 5H), 7.22˜7.28 (m, 1H), 7.11˜7.20 (m, 3H), 6.80˜6.86 (m, 1H), 6.65 (t, J=6.4 Hz, 1H), 4.48 (dd, J=8.0 Hz, 1H), 4.51 (d, J=12.0 Hz, 1H), 4.46 (d, J=12.0 Hz, 1H), 3.55˜3.62 (m, 1H), 3.25˜3.33 (m, 1H), 2.15˜2.23 (m, 1H), 2.02˜2.12 (m, 1H). MS (M+H)+: 409.

Workup

concentrationThen it was concentrated in vacuo
customthe resulting residue was purified

Sources & evidence

ORD record: ord-23015343443f45ab81bbb2b0de8044d6
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265773B2

Reaction notes

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