2-(Tributylstannyl)pyrazine → HCID 46202080, compound

HRID 1662251Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:34]1[CH:39]=[N:38][CH:37]=[CH:36][N:35]=1)CCC>CN(C=O)C.[Cl-].[Na+].O.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>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[C:10]([NH2:18])=[N:9][C:8]2([C:4]1[CH:3]=[CH:2][CH:7]=[C:6]([C:34]2[CH:39]=[N:38][CH:37]=[CH:36][N:35]=2)[CH:5]=1)[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=1

Participants

Conditions

Temperature: 180 °C

Procedure

1-(3-Bromophenyl)-4-fluoro-1-(2-(trifluoromethyl)pyridin-4-yl)-1H-isoindol-3-amine (131 mg, 0.29 mmol), 2-(tributylstannyl)pyrazine (0.096 mL, 0.31 mmol) and Pd(Ph3P)4 (33.6 mg, 0.03 mmol) were dissolved in DMF (2 mL) and the reaction mixture was heated in a microwave reactor at 180° C. for 15 min. Brine was added and the mixture was extracted with EtOAc (3×). The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo. Purification by preperative HPLC afforded the title compound 18 mg (14% yield).

Workup

extractionthe mixture was extracted with EtOAc (3×)
dry with materialThe combined organic phases were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by preperative HPLC

Sources & evidence

ORD record: ord-efaccc7c113e4049a115bda414c8a44f
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030500B2

Reaction notes

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