Ethanol → 4'-[(5-Iodopyrimidin-4-yl)amino]-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

HRID 77712Notes

Reaction equation

HRID 77712 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)=[O:16])[CH:9]=2)=[CH:4][CH:3]=1.Cl[C:29]1[C:34]([I:35])=[CH:33][N:32]=[CH:31][N:30]=1.C(O)C.C([O-])([O-])=O.[Na+].[Na+]>>[I:35][C:34]1[C:29]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([C:15]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=4)=[O:16])[CH:9]=3)=[CH:4][CH:3]=2)=[N:30][CH:31]=[N:32][CH:33]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 112302044-Chloro-5-iodopyrimidineHCID 690431094'-Amino-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

Product 1

HCID 690435614'-[(5-Iodopyrimidin-4-yl)amino]-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamideYield 44.3%

Procedure

4′-Amino-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide (0.26 g, 0.00070 mol) was mixed with 4-chloro-5-iodopyrimidine (0.17 g, 0.00070 mol) in ethanol (3.00 mL, 0.0514 mol) and the mixture was heated to reflux for 2 hours at which time LCMS analysis showed mainly product. To the reaction was added sat. Na2CO3 solution and the mixture was extracted with ethyl acetate. The organic extracts were washed with water, saturated NaCl, dried (MgSO4) and concentrated in vacuo. The concentrate was chromatographed on silica gel using 30% EtOAc/hexanes to give the product (178 mg, 44% yield). 1H NMR (CDCl3): δ□ 8.66 (s, 1H), 8.62 (s, 1H), 7.96 (m, 2H), 7.70-7.89 (m, 5H), 7.37-7.50 (m, 5H), 7.20 (s, 1H), 2.38 (s, 3H). MS (EI) m/z=575 (M+H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours at which time LCMS analysis
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic extracts were washed with water, saturated NaCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe concentrate was chromatographed on silica gel using 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-237774e7c0004c8aaf7d4062ea9e9cb8
Source dataset
uspto-grants-2014_09
Patent number
US08841318B2

Reaction notes

Loading…