Triethylamine → HCID 67111749, compound

HRID 1177550Notes

Reaction equation

C(N(CC)CC)C.[O:8]1[CH2:13][CH2:12][CH2:11][O:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27](Br)[CH:26]=[CH:25][C:23]=3[N:24]=2)=[C:16]([F:30])[CH:15]=1.C[CH2:32][O:33][C:34](C)=[O:35]>CN(C=O)C.C1COCC1.CO>[O:8]1[CH2:13][CH2:12][CH2:11][O:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27]([C:34]([O:33][CH3:32])=[O:35])[CH:26]=[CH:25][C:23]=3[N:24]=2)=[C:16]([F:30])[CH:15]=1

Participants

Conditions

Temperature: 95 °C

Procedure

Triethylamine (0.32 mL, 2.28 mmol), 1,3-(bis[diphenylphosphino]propane) dichloropalladium(II) (0.051 g, 0.076 mmol), and 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-bromobenzo[d]thiazole (0.75 g, 1.90 mmol) were mixed in DMF:THF:MeOH (2:7:2, 11 mL total volume) in a heavy-walled pressure tube. The tube was placed under CO atmosphere (20 psi) and then heated to 95° C. for 16 h. The mixture was cooled to RT and EtOAc (5 mL) was added. The suspension was filtered and the collected solid was washed with EtOAc. The solid obtained was then partitioned between DCM and water, the layers were separated, and the organic layer was dried (MgSO4) and concentrated under vacuum to give methyl 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylate as a white solid.

Workup

temperatureThe mixture was cooled to RT
filtrationThe suspension was filtered
washthe collected solid was washed with EtOAc
customThe solid obtained
customwas then partitioned between DCM and water
customthe layers were separated
dry with materialthe organic layer was dried (MgSO4)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-a7fd57d762c940adb4d23427f774e080
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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