N-Methylethylamine → HCID 136375863, compound

HRID 2047309Notes

Reaction equation

HRID 2047309 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[C:17]([CH3:19])[C:16]([OH:20])=[C:15]([CH3:21])[CH:14]=3)[N:9]=2)[CH:5]=[C:4]([CH3:22])[N:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH2:65]([NH:67][CH3:68])[CH3:66]>CC(=O)OCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:65]([N:67]([CH3:68])[C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[C:17]([CH3:19])[C:16]([OH:20])=[C:15]([CH3:21])[CH:14]=3)[N:9]=2)[CH:5]=[C:4]([CH3:22])[N:3]=1)[CH3:66]

Participants

6

Reactant 3

HCID 12219N-MethylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 135964207HCID 135964207, compound

Product 1

HCID 136375863HCID 136375863, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[5-(2-chloro-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenol (549 mg, 1.74 mmol) and Na tert.-butylate (346 mg, 3.60 mmol) in ethyl-methylamine (10 mL), Xantphos (106 mg, 0.18 mmol) and Pd(OAc)2 (47 mg, 0.21 mmol) is added. The mixture is stirred in an autoclave at 80° C. for 24 h. The dark mixture is cooled to rt, diluted with EA (200 mL), washed three times with sat. aq. NaHCO3-solution, dried over MgSO4, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with EA containing 20% of methanol to give 4-{5-[2-(ethyl-methyl-amino)-6-methyl-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-2,6-dimethyl-phenol (119 mg) as a yellow solid; LC-MS: tR=0.83 min; [M+1]+=339.10; 1H NMR (D6-DMSO): δ 1.12 (m, 3H), 2.26 (s, 6H), 2.43 (s, 3H), 2.88-2.98 (m, 2H), 3.07 (s, 3H), 7.00 (s, 1H), 7.08 (s, 1H), 7.67 (s br, 1H), 7.68 (s, 1H), 8.94 (s br, 1H).

Workup

  1. temperatureThe dark mixture is cooled to rt
  2. washwashed three times with sat. aq. NaHCO3-solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by MPLC on silica gel eluting with EA containing 20% of methanol

Sources & evidence

ORD record
ord-e3cd0060c2e8416b93928565aa70ec38
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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