3-Bromopyridine → (4-Methyl-pyridin-2-yl)-[6-(2-pyridin-3-yl-oxazol-5-yl)-pyridin-2-yl]-amine

HRID 1854595Notes

Reaction equation

HRID 1854595 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[O:19][C:18]([CH:20]=[CH:21][C:22]4[CH:29]=CC(C#N)=CC=4)=[N:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=1.CC1C=C[N:34]=[C:33](NC2C=CC=C(C3OC=NC=3)N=2)C=1.BrC1C=NC=CC=1.O(C(C)(C)C)[Li]>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.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([C:15]3[O:19][C:18]([C:20]4[CH:33]=[N:34][CH:29]=[CH:22][CH:21]=4)=[N:17][CH:16]=3)[N:14]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 122863-BromopyridineHCID 53311228(4-Methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amineHCID 673240684-(2-{5-[6-(4-Methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-vinyl)-benzonitrileHCID 178506942HCID 178506942, compound

Product 1

HCID 67325852(4-Methyl-pyridin-2-yl)-[6-(2-pyridin-3-yl-oxazol-5-yl)-pyridin-2-yl]-amineYield 8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Prepared as for 4-(2-{5-[6-(4-methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-vinyl)-benzonitrile above using (4-methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amine, 3-bromopyridine, Pd(PPh3)4, LiOtBu and anhydrous 1,4-dioxane to afford the title compound as a pale yellow solid (8%). 1H NMR (300 MHz, DMSO-d6) δ=9.81 (s, 1H), 9.31 (s, 1H), 8.76 (d, J=4.8 Hz, 1H), 8.46 (d, J=8.1 Hz, 1H), 8.12 (d, J=5.0 Hz, 1H), 7.91 (s, 2H), 7.84-7.76 (m, 1H), 7.69-7.52 (m, 2H), 7.45 (d, J=7.4 Hz, 1H), 6.79 (d, J=5.0 Hz, 1H), 2.36 (s, 3H). (ESI+) m/z 330 (M+H).

Sources & evidence

ORD record
ord-604967d1f2ce480c8b1089d5314e7a94
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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