Hydrochloric Acid → (S)-[2,3'-Bipyridin]-2'-yl(4-(trifluoromethyl)phenyl)-methanaminedihydrochloride

HRID 1622562Notes

Reaction equation

C(OC(=O)[NH:7][C@H:8]([C:19]1[C:24](Br)=[CH:23][CH:22]=[CH:21][N:20]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)(C)(C)C.C([Sn](CCCC)(CCCC)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)CCC.[ClH:46]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[ClH:46].[ClH:46].[N:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[C:24]1[C:19]([C@H:8]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([F:17])([F:16])[F:18])=[CH:13][CH:14]=2)[NH2:7])=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of (S)-tert-butyl(3-bromopyridin-2-yl)(4-(trifluoromethyl)-phenyl)methylcarbamate (Intermediate 40, Step 5) (0.711 g, 1.649 mmol), 2-(tributylstannyl)pyridine (0.910 g, 2.473 mmol), and (Ph3P)4Pd (0.381 g, 0.330 mmol) in 1,4-dioxane (10 mL) was heated by microwave at 125° C. for 30 min. The reaction mixture was then cooled, concentrated, and purified by ISCO (silica gel, 0-60% EtOAc/hexanes). The residue was dissolved in DCM (3 mL) and hydrogen chloride (3.30 mL, 13.19 mmol, 4.0 M in 1,4-dioxane) was added. After stirring for 2 h, the mixture was concentrated to dryness to give the title compound. MS (ESI pos. ion) m/z: 330.0 (M+H).

Workup

temperatureThe reaction mixture was then cooled
concentrationconcentrated
custompurified by ISCO (silica gel, 0-60% EtOAc/hexanes)
dissolutionThe residue was dissolved in DCM (3 mL)
concentrationthe mixture was concentrated to dryness

Sources & evidence

ORD record: ord-5905962cd45b4ceeb7c5955a5e3f1e4c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778941B2

Reaction notes

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