Methanol → 6-Bromo-7-fluoro-2'-methyl-2-phenyl-2'h-spiro[chroman-4,5'-[1,2,4]oxadiazol]-3'-amine

HRID 2096600Notes

Reaction equation

HRID 2096600 reaction equation
Cl.[CH3:2][NH:3][OH:4].CO[Na].[Br:8][C:9]1[CH:10]=[C:11]2C(=[CH:17][C:18]=1[F:19])O[CH:14]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:13][C:12]2=[N:26][C:27]#[N:28].[CH3:29][OH:30]>>[Br:8][C:9]1[CH:10]=[C:11]2[C:12]3([O:4][N:3]([CH3:2])[C:27]([NH2:28])=[N:26]3)[CH2:13][CH:14]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:30][C:29]2=[CH:17][C:18]=1[F:19]

Participants

5

Reactant 4

HCID 887MethanolHCID 77906N-methylhydroxylamine hydrochlorideHCID 58423885N-(6-bromo-7-fluoro-2-phenylchroman-4-ylidene)cyanamideHCID 178418582HCID 178418582, compound

Product 1

HCID 584242966-Bromo-7-fluoro-2'-methyl-2-phenyl-2'h-spiro[chroman-4,5'-[1,2,4]oxadiazol]-3'-amineYield 30%

Procedure

To a solution of N-methyl-hydroxylamine hydrochloride (35 mg, 0.355 mmol) in MeOH (5 mL) was added MeONa (0.07 mL, 25% (Wt.) in MeOH), followed by N-(6-bromo-7-fluoro-2-phenylchroman-4-ylidene)cyanamide (122 mg, 0.355 mmol). After stirred for 10 minutes, the solvent was removed in vacuo. The residue was purified by preparative TLC to give 6-bromo-7-fluoro-2′-methyl-2-phenyl-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazol]-3′-amine (30 mg, 30%). 1H-NHR (MeOD): 2.18 (m, 1H), 2.33 (m, 1H), 3.08 (d, 3H), 5.28 (m, 1H), 6.75 (m, 1H), 7.38 (m, 5H), 7.61 (m, 1H).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-a679a5dbaebb41e3a6f37e4c1a5229e0
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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