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1,4-Dioxane → 4-(2-{5-[6-(4-Methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-vinyl)-benzonitrile

HRID 1854593
Notes
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Reaction equation

HRID 1854593 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[O:19][CH:18]=[N:17][CH:16]=3)[N:10]=2)[CH:3]=1.Br[CH:21]=[CH:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1.O(C(C)(C)C)[Li].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:10]=[C:11]([C:15]3[O:19][C:18]([CH:21]=[CH:22][C:23]4[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=4)=[N:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 53311228(4-Methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amineHCID 714006384-(2-Bromovinyl)-benzonitrileHCID 178506942HCID 178506942, compound

Product 1

HCID 673240684-(2-{5-[6-(4-Methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-vinyl)-benzonitrileYield 25.3%

Reagents, catalysts & solvents

2
HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A sealed tube was charged with a mixture of (4-methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amine (200 mg, 0.793 mmol), 4-(2-bromovinyl)-benzonitrile (330 mg, 1.59 mmol), Pd(PPh3)4 (46 mg, 0.0396 mmol), LiOtBu (127 mg, 1.59 mmol) and anhydrous 1,4-dioxane (5 ml) and heated to 100° C. with stirring for 2 h. The cooled reaction mixture was treated with water and extracted with DCM. The combined organics were dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on SiO2, eluting with 50% EtOAc in cyclohexane to afford the title compound as a yellow solid (76 mg, 25%). 1H NMR (300 MHz, DMSO-d6) δ=9.79 (s, 1H), 8.12 (d, J=5.1 Hz, 1H), 7.97 (d, J=8.3 Hz, 2H), 7.90 (d, J=8.2 Hz, 2H), 7.86-7.61 (m, 5H), 7.46 (d, J=16.3 Hz, 1H), 7.36 (d, J=7.3 Hz, 1H), 6.78 (d, J=4.7 Hz, 1H), 2.35 (s, 3H). (ESI+) m/z 380 (M+H).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with DCM
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure before purification by column chromatography on SiO2
  6. washeluting with 50% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-d2f8f8cfa30b4a99915291f4d919c6ba
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08962665B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes