tert-Butanol → 7-[5-(1-Ethenylcyclopropyl)-3-pyridinyl]-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoline

HRID 1521616Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[N:13][N:14]=[C:7]1[CH2:6][CH2:5]2.[CH:15]([C:17]1([C:20]2[CH:21]=[C:22](B(O)O)[CH:23]=[N:24][CH:25]=2)[CH2:19][CH2:18]1)=[CH2:16].C(=O)([O-])[O-].[K+].[K+].C(O)(C)(C)C>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl.O>[CH:15]([C:17]1([C:20]2[CH:21]=[C:22]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]3[CH:12]=[N:13][N:14]=[C:7]3[CH2:6][CH2:5]4)[CH:23]=[N:24][CH:25]=2)[CH2:19][CH2:18]1)=[CH2:16]

Participants

Conditions

Temperature: 80 °C

Procedure

To a vial containing the title compound from Example 22 Step B (35 mg, 0.14 mmol), the title compound from Example 73 Step D (30 mg, 0.16 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (2.0 mg, 2.8 μmol), and potassium carbonate 285 mg, 0.42 mmol) was added tert-butanol (1.6 mL) and water (0.19 mL). The vial was flushed with nitrogen, sealed tightly and heated to 80° C. overnight. The reaction solution was then cooled to room temperature and concentrated under reduced pressure to provide the title compound: LCMS m/z 315.05 [M+H]+.

Workup

customThe vial was flushed with nitrogen
customsealed tightly
temperatureThe reaction solution was then cooled to room temperature
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d6943f69094b4fbe866d498218a0ed60
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073929B2

Reaction notes

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