Potassium Carbonate → N-(4'-amino-biphenyl-2-ylmethyl)-2,2,2-trifluoro-acetamide

HRID 74092Notes

Reaction equation

Br[C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8].CC1(C)C(C)(C)OB([C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)O1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:28][C:27]1[CH:29]=[CH:30][C:24]([C:2]2[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=2[CH2:4][NH:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-(2-bromo-benzyl)-2,2,2-trifluoro-acetamide (282 mg, 1.0 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (284 mg, 1.3 mmol), Pd(OAc)2 (20 mg, 0.09 mmol) and PS—PPh3 (40 mg, 3 mmol/g, 0.12 mmol) was dissolved in DMF (5 mL) and 4M K2CO3 solution (0.5 mL) was added. The reaction was heated at 80° C. overnight. The mixture was filtered, concentrated and purified by column chromatography (0-50% ethyl acetate-hexanes) to yield N-(4′-amino-biphenyl-2-ylmethyl)-2,2,2-trifluoro-acetamide (1-1) (143 mg, 49%). HPLC ret. time 1.90 min, 10-99% CH3CN, 5 min run; ESI-MS 295.5 m/z (MH+).

Workup

filtrationThe mixture was filtered
concentrationconcentrated
custompurified by column chromatography (0-50% ethyl acetate-hexanes)

Sources & evidence

ORD record: ord-28c5a75698bd4acf8452811649238cf7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829204B2

Reaction notes

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