Sodium Carbonate → HCID 118092832, compound

HRID 2207420Notes

Reaction equation

HRID 2207420 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[N:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=2)[CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.[CH2:28]([O:30][C:31](=[O:41])[CH:32]=[CH:33][C:34]1[CH:39]=[CH:38][C:37](Br)=[CH:36][N:35]=1)[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[CH2:28]([O:30][C:31](=[O:41])[CH:32]=[CH:33][C:34]1[CH:39]=[CH:38][C:37]([C:6]2[CH:5]=[C:4]([NH:17][C:18]3[N:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[CH:20][N:19]=3)[CH:3]=[C:2]([CH3:1])[CH:7]=2)=[CH:36][N:35]=1)[CH3:29]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 58456089N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amineHCID 67058999Ethyl 3-(5-Bromo-2-pyridyl)acrylate

Product 1

HCID 118092832HCID 118092832, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (222 mg, 0.585 mmol), ethyl-3-(5-bromopyridin-2-yl)prop-2-enoate (101 mg, 0.393 mmol), PdCl2(dppf) (62.9 mg, 0.086 mmol), sodium carbonate (2 M, 0.40 mL, 0.800 mmol), and dioxane (2.00 mL) was purged and flushed with Ar(g) (3×) and irradiated in a microwave reactor for 10 minutes at 100° C. The reaction mixture was further irradiated with microwave at 150° C. for another 10 minutes. The mixture was filtered, concentrated under reduced pressure and the residue was purified by silica gel chromatography (20% ethyl acetate in hexanes) to afford ethyl-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]prop-2-enoate. C22H20F3N4O2 [M+H]+ 429. found 429. 1H NMR (500 MHz, CDCl3) δ 8.89 (d, J=2.1 Hz, 1H), 8.64 (d, J=4.9 Hz, 1H), 7.93-7.85 (m, 2H), 7.73 (d, J=15.7 Hz, 1H), 7.64 (s, 1H), 7.48 (d, J=8.1 Hz, 1H), 7.36 (s, 1H), 7.13 (s, 1H), 7.03 (d, J=4.9 Hz, 1H), 6.94 (d, 1H), 4.28 (q, J=7.1 Hz, 2H), 2.42 (s, 3H), 1.34 (t, J=7.1 Hz, 3H).

Workup

  1. customwas purged
  2. customflushed with Ar(g) (3×)
  3. customirradiated in a microwave reactor for 10 minutes at 100° C
  4. customThe reaction mixture was further irradiated with microwave at 150° C. for another 10 minutes
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9524d2ec2fdc492ea7967431e55f32b3
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

Loading…