Water → HCID 136003665, compound

HRID 538551Notes

Reaction equation

HRID 538551 reaction equation
[F:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=[C:4]([F:23])[C:3]=1[C:24]([NH2:26])=[O:25].O>C(Cl)Cl>[F:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=[C:4]([F:23])[C:3]=1[C:24]([NH2:26])=[O:25]

Participants

4

Reactant 2

HCID 962WaterHCID 59402683HCID 59402683, compound

Product 1

HCID 136003665HCID 136003665, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bororn tribromide solution (1.0 M in CH2Cl2, 1.5 ml, 1.5 mmol, 2 equiv.) was added slowly, dropwise to stirred suspension of 2,6-difluoro-3-[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]methoxybenzenecarboxamide (272 mg, 0.75 mmol, 1 equiv.) in CH2Cl2 (5 ml), at r.t., under N2. The reaction mixture was stirred at r.t. for 4 h and poured into water (20 ml). CH2Cl2 (10 ml) was added and the biphasic mixture was stirred for 30 min. at r.t. The white un-dissolved solid was filtered, washed with water and Et2O, to give 170 mg (65% yield), mp 209-210° C., HPLC-MS (method 1): m/z 348 [M+H]+, Rt=3.00 min.

Workup

  1. customat r.t.
  2. stirringThe reaction mixture was stirred at r.t. for 4 h
  3. stirringthe biphasic mixture was stirred for 30 min. at r.t
  4. dissolutionThe white un-dissolved solid
  5. filtrationwas filtered
  6. washwashed with water and Et2O
  7. customto give 170 mg (65% yield), mp 209-210° C., HPLC-MS (method 1)

Sources & evidence

ORD record
ord-c2b6b13b30f04e729ae0394f774996b3
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

Loading…