Ethanamine, 2,2,2-trifluoro- → HCID 57785701, compound

HRID 1893681Notes

Reaction equation

[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].[Li]CCCC.[Cl:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[C:20](S(CC)(=O)=O)[CH:19]=[C:18]2[O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1>O1CCCC1>[Cl:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[C:20]([NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])[CH:19]=[C:18]2[O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In a pre-dried 3-necked round bottom flask was dissolved 2,2,2-trifluoro-ethylamine (91 mg, 0.92 mmol, 1.2 equiv) in dry tetrahydrofuran (0.5 mL), under a nitrogen atmosphere. The flask was cooled down to −78° C. and 2.5M n-BuLi in hexanes (428 μL, 1.07 mmol, 1.4 equiv) was added via syringe. The mixture was stirred for 5 minutes then gradually warmed to 0° C. At this point, 8-chloro-2-ethanesulfonyl-4-(4-methoxy-benzyloxy)-quinoline (300 mg, 0.766 mmol, 1 equiv) in a solution of THF was slowly added. The mixture was stirred for 17 h at room temperature then quenched with brine and extracted into dichloromethane. The organic layer was dried over MgSO4 and concentrated down in vacuo to afford [8-chloro-4-(4-methoxy-benzyloxy)-quinolin-2-yl]-(2,2,2-trifluoro-ethyl)-amine (203 mg, 67% yield). LCMS found 397.11 [M+H]+.

Workup

temperaturethen gradually warmed to 0° C
stirringThe mixture was stirred for 17 h at room temperature
customthen quenched with brine
extractionextracted into dichloromethane
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated down in vacuo

Sources & evidence

ORD record: ord-939e63aebddd441f868d2c5caddbd299
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513186B2

Reaction notes

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