Potassium Carbonate → {6-[2-(2-Methoxy-pyridin-3-yl)-oxazol-5-yl]-pyridin-2-yl}-(4-methyl-pyridin-2-yl)-amine

HRID 1854615Notes

Reaction equation

HRID 1854615 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[N:37]=[C:36]([NH:38][C:39]3[CH:44]=[C:43]([CH3:45])[CH:42]=[CH:41][N:40]=3)[CH:35]=[CH:34][CH:33]=2)=[CH:30][N:31]=1.[CH3:46][O:47][C:48]1[C:53](B(O)O)=[CH:52][CH:51]=[CH:50][N:49]=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>[CH3:46][O:47][C:48]1[C:53]([C:27]2[O:28][C:29]([C:32]3[N:37]=[C:36]([NH:38][C:39]4[CH:44]=[C:43]([CH3:45])[CH:42]=[CH:41][N:40]=4)[CH:35]=[CH:34][CH:33]=3)=[CH:30][N:31]=2)=[CH:52][CH:51]=[CH:50][N:49]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 53311312HCID 53311312, compoundHCID 67323426(4-Methyl-pyridin-2-yl)-[6-(2-phenyl-oxazol-5-yl)-pyridin-2-yl]-amine

Product 1

HCID 53312248{6-[2-(2-Methoxy-pyridin-3-yl)-oxazol-5-yl]-pyridin-2-yl}-(4-methyl-pyridin-2-yl)-amine

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 [6-(2-iodo-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine, 2-methoxy-pyridine-3-boronic acid, K2CO3 and Pd(PPh3)4 in a 2:1 mixture by volume of THF and water to give {6-[2-(2-methoxy-pyridin-3-yl)-oxazol-5-yl]-pyridin-2-yl}-(4-methyl-pyridin-2-yl)-amine as a yellow solid. 1-1 NMR (400 MHz, DMSO-d6) δ 9.76 (s, 1H), 8.46-8.31 (m, 2H), 8.12 (d, J=5.0 Hz, 1H), 7.87-7.82 (m, 2H), 7.82-7.75 (m, 1H), 7.63 (d, J=8.4 Hz, 1H), 7.34 (d, J=7.3 Hz, 1H), 7.21 (dd, J=7.5, 5.0 Hz, 1H), 6.78 (d, J=5.0 Hz, 1H), 4.04 (s, 3H), 2.33 (s, 3H). (ESI+) m/z 360 (M+H)+. Retention time=2.54 mins (method 1).

Sources & evidence

ORD record
ord-195c237b9b7b46ecb3692c29c31a730d
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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