Aniline → HCID 57742714, compound

HRID 911878Notes

Reaction equation

HRID 911878 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:14][C:15]1[CH:16]=[C:17]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:18]([NH:21][C:22]2[S:23][CH:24]=[C:25]([CH2:27]Cl)[N:26]=2)=[N:19][CH:20]=1>CN1C(=O)CCC1>[Br:14][C:15]1[CH:16]=[C:17]([O:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:18]([NH:21][C:22]2[S:23][CH:24]=[C:25]([CH2:27][NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:26]=2)=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 10796Cesium carbonateHCID 57742594HCID 57742594, compound

Product 1

HCID 57742714HCID 57742714, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Aniline (0.0352 g, 0.378 mmol) was dissolved in 2 mL NMP at ambient temperature. Cs2CO3 (0.0246 g, 0.0756 mmol) and solid 5-bromo-N-(4-(chloromethyl)thiazol-2-yl)-3-phenoxypyridin-2-amine (0.030 g, 0.0756 mmol) were added to the reaction and the mixture was stirred at ambient temperature overnight. The reaction was concentrated to dryness, dissolved in CH2Cl2, washed with water, dried over Na2SO4, and concentrated to dryness. The residue was purified by preparative HPLC to give the title compound (0.010 g, 29.2% yield) as tan solids. 1H NMR (CDCl3) δ 4.34 (br s, 3H), 6.67-6.74 (m, 4H), 7.07 (d, J=8.0 Hz, 2H), 7.13 (d, J=1.8 Hz, 1H), 7.18 (t, J=7.7 Hz, 2H), 7.24-7.27 (m, 1H), 7.43 (t, J=7.9 Hz, 2H), 8.13 (d, J=1.6 Hz, 1H), 8.74 (br s, 1H).

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d0ae3af195f14bae924e856133acf28a
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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