Potassium Carbonate → (4-Methyl-pyridin-2-yl)-(3-{2-[2-(3-trifluoromethyl-phenyl)-vinyl]-oxazol-5-yl}-phenyl)-amine

HRID 1854614Notes

Reaction equation

HRID 1854614 reaction equation
CC1C=CN=C(NC2C=CC=C(C3OC(C4C=CC=CC=4)=NC=3)N=2)C=1.I[C:27]1[O:28][C:29]([C:32]2[CH:33]=[C:34]([NH:38][C:39]3[CH:44]=[C:43]([CH3:45])[CH:42]=[CH:41][N:40]=3)[CH:35]=[CH:36][CH:37]=2)=[CH:30][N:31]=1.[F:46][C:47]([F:60])([F:59])[C:48]1[CH:49]=[C:50](/[CH:54]=[CH:55]/B(O)O)[CH:51]=[CH:52][CH:53]=1.C([O-])([O-])=O.[K+].[K+]>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.C1COCC1>[CH3:45][C:43]1[CH:42]=[CH:41][N:40]=[C:39]([NH:38][C:34]2[CH:35]=[CH:36][CH:37]=[C:32]([C:29]3[O:28][C:27]([CH:55]=[CH:54][C:50]4[CH:51]=[CH:52][CH:53]=[C:48]([C:47]([F:46])([F:59])[F:60])[CH:49]=4)=[N:31][CH:30]=3)[CH:33]=2)[CH:44]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 451566922-(3-Trifluoromethyl-phenyl)-etheneboronic acidHCID 67323426(4-Methyl-pyridin-2-yl)-[6-(2-phenyl-oxazol-5-yl)-pyridin-2-yl]-amineHCID 67325433[3-(2-Iodo-oxazol-5-yl)-phenyl]-(4-methyl-pyridin-2-yl)-amine

Product 1

HCID 67323828(4-Methyl-pyridin-2-yl)-(3-{2-[2-(3-trifluoromethyl-phenyl)-vinyl]-oxazol-5-yl}-phenyl)-amineYield 72%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared as for (4-methyl-pyridin-2-yl)-[6-(2-phenyl-oxazol-5-yl)-pyridin-2-yl]-amine above using [3-(2-Iodo-oxazol-5-yl)-phenyl]-(4-methyl-pyridin-2-yl)-amine, trans-2-(3-trifluoromethylphenyl)vinylboronic acid, K2CO3 and Pd(PPh3)4 in a 2:1 mixture by volume of THF and water to give (4-methyl-pyridin-2-yl)-(3-{2-[2-(3-trifluoromethyl-phenyl)-vinyl]-oxazol-5-yl}-phenyl)-amine as a pale yellow solid (72%). 1H NMR (400 MHz, DMSO-d6) δ 9.26-8.94 (m, 1H), 8.15 (s, J=8.6 Hz, 1H), 8.11-8.06 (m, 3H), 7.76-7.63 (m, 5H), 7.43 (d, J=16.5 Hz, 1H), 7.40-7.29 (m, 2H), 6.68 (s, 1H), 6.64 (d, J=5.2 Hz, 1H), 2.25 (s, 3H). (ESI+) m/z 422 (M+H)+. Retention time=3.84 mins (method 1).

Sources & evidence

ORD record
ord-f56ea6772f4649869343259cb2435820
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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