Cesium carbonate → HCID 58204251, compound

HRID 2385838Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:23][C:22]3[C:21]4[N:24]=[C:25]([N:28]5[CH2:33][C@H:32]([CH3:34])[NH:31][C@H:30]([CH3:35])[CH2:29]5)[CH:26]=[CH:27][C:20]=4[O:19][CH2:18][CH2:17][C:16]=3[CH:15]=2)=[N:12][CH:11]=[N:10]1.Br[CH2:37][CH2:38]F.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:23][C:22]3[C:21]4[N:24]=[C:25]([N:28]5[CH2:33][C@H:32]([CH3:34])[N:31]([CH2:37][CH3:38])[C@H:30]([CH3:35])[CH2:29]5)[CH:26]=[CH:27][C:20]=4[O:19][CH2:18][CH2:17][C:16]=3[CH:15]=2)=[N:12][CH:11]=[N:10]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-[2-(2,4-Difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-9-((3R,5S)-3,5-dimethyl-piperazin-1-yl)-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulene (150 mg 0.3 mmol), 1-Bromo-2-fluoro-ethane (65 mg, 0.45 mmol) and Cesium carbonate (200 mg, 0.6 mmol) in N,N-Dimethyl-formamide (2 mL) was stirred at 120° C. for 1 h under the irradiation of microwave. The reaction mixture was filtered over celite and purified by pre-TLC (Hexanes/EtOAc=1:1) to afford 314 Yield=56%. 1H NMR (CDCl3, 400 MHz): δ8.02 (s, 1 H), 7.49-7.46 (m, 1 H), 7.11-6.97 (m, 4 H), 6.45 (d, J=8.8 Hz, 1 H), 4.18 (t, J=4.8 Hz, 2 H), 3.86 (d, J=11.6 Hz, 2 H), 3.07 (t, J=4.8 Hz, 2H), 2.96 (q, J1=7.2 Hz, J2=5.2 Hz, 2 H), 2.64-2.51 (m, 4 H), 1.13 (d, J=6.0 Hz, 6 H), 0.88-0.81 (m, 3H). ESI-MS: m/z=523 [M+H+]

Workup

filtrationThe reaction mixture was filtered over celite
custompurified by pre-TLC (Hexanes/EtOAc=1:1)

Sources & evidence

ORD record: ord-2a1fbd1166564768adc149be07aa88de
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263633B2

Reaction notes

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