2-Methyl-2-butene → HCID 24826062, compound

HRID 910931Notes

Reaction equation

HRID 910931 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH3:19])[N:18]=2)[CH:8]=1.BrB(Br)Br.CC(=CC)C.C([O-])(O)=O.[Na+]>O.ClCCl>[CH3:19][C:17]1[N:18]=[C:14]([NH:13][C:9]2[CH:8]=[C:7]([O:6][C:5]3[CH:4]=[C:3]([OH:2])[CH:22]=[CH:21][CH:20]=3)[CH:12]=[CH:11][N:10]=2)[S:15][CH:16]=1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 24827110HCID 24827110, compound

Product 1

HCID 24826062HCID 24826062, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 50 mL round bottom flask was charged with 4-(3-methoxyphenoxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (0.2 g, 0.638 mmol) and dichloromethane (6 mL). The solution was cooled to 0° C., and tribromoborane (0.181 mL, 1.91 mmol) and 1 mL of 2-methyl-2-butene were added. The reaction mixture was stirred at 0° C. for 1 hour. Water and saturated solution of NaHCO3 were added, and the reaction mixture was extracted with EtOAc. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified on a prepacked silica gel column eluting with 20-35% ethyl acetate in hexanes to give 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)phenol (0.124 g, 64.3% yield) as light orange solid. 1H NMR (DMSO) δ 10.98 (bs, 1H), 9.78 (bs, 1H), 8.15 (d, 1H), 7.26 (t, 1H), 6.69 (ddd, 1H), 6.56 (m, 2H), 6.51 (m, 3H), 2.20 (d, 3H); Mass spectrum (esi) m/z 300 (100) (M+H).

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on a prepacked silica gel column
  6. washeluting with 20-35% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-47cd170ca5bb457c9a58a40398bca7c2
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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