Water → [6-(2-Benzoxazole-2-yl-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine

HRID 1854618Notes

Reaction equation

HRID 1854618 reaction equation
I[C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.[O:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[CH:22]1.O(C(C)(C)C)[Li].O>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:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 9228BenzoxazoleHCID 53311312HCID 53311312, compoundHCID 178506942HCID 178506942, compound

Product 1

HCID 53312246[6-(2-Benzoxazole-2-yl-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amineYield 12.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A sealed tube with a teflon screw cap was charged with a mixture of [6-(2-iodo-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine (100 mg, 0.264 mmol), benzoxazole (31 mg, 0.264 mmol), Pd(PPh3)4 (15 mg, 0.013 mmol) and LiOtBu (42 mg, 0.529 mmol) in dry dioxane (5 ml) and heated to 100° C. for 24 h. The cooled 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 30% EtOAc in cyclohexane to afford the title compound as a beige solid (12 mg, 12%). 1H NMR (400 MHz, DMSO-d6) δ 9.88 (s, 1H), 8.14-8.11 (m, 2H), 7.99-7.88 (m, 3H), 7.83 (t, J=7.9 Hz, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.61-7.51 (m, 2H), 7.46 (d, J=7.3 Hz, 1H), 6.80 (d, J=5.0 Hz, 1H), 2.41 (s, 3H). (ESI+) m/z 370 (M+H)+. Retention time=2.88 mins (method 1).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure before purification by column chromatography on SiO2 eluting with 30% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-86f11d124dca4080933a977e4ceece23
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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