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Diethylamine → HCID 58418005, compound

HRID 1908858
Notes
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Reaction equation

HRID 1908858 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=3)[N:9]=2)[CH:5]=[C:4]([CH3:20])[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:27]([NH:29][CH2:30][CH3:31])[CH3:28].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>O1CCOCC1>[CH2:27]([N:29]([CH2:30][CH3:31])[C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=3)[N:9]=2)[CH:5]=[C:4]([CH3:20])[N:3]=1)[CH3:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86657320HCID 86657320, compound

Product 1

HCID 58418005HCID 58418005, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-chloro-4-[3-(2-methyl-4-pyridinyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridine (160 mg, 0.558 mmol, Example 43a)) in dioxane (10 mL), Cs2CO3 (636 mg, 1.95 mmol) and diethylamine (204 mg, 2.79 mmol) is added. The mixture is degassed and put under N2 before Pd(II) acetate (25 mg, 0.112 mmol) and Xantphos (116 mg, 0.201 mmol) is added. The mixture is stirred in a sealed vial at 90° C. for 72 h before it is cooled to rt. The mixture is filtered and the filtrate is evaporated. The crude product is purified on prep. TLC plates with heptane:EA 3:1 to give 2-diethylamino-4-[3-(2-methyl-4-pyridinyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridine (43 mg) as a yellow solid; LC-MS: tR=0.66 min, [M+1]+=324.15; 1H NMR δ 1.26 (t, J=7.0 Hz, 6H), 2.51 (s, 3H), 2.71 (s, 3H), 3.63 (q, J=7.0 Hz, 4H), 7.01 (s, 1H), 7.09 (s, 1H), 7.86 (d, J=5.0 Hz, 1H), 7.94 (s, 1H), 8.71 (d, J=5.0 Hz, 1H).

Workup

  1. customThe mixture is degassed
  2. additionis added
  3. temperatureis cooled to rt
  4. filtrationThe mixture is filtered
  5. customthe filtrate is evaporated
  6. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-ed8fdbe4d52145f1804168c9225f0b1b
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598208B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes