Potassium Carbonate → HCID 67323295, compound

HRID 1854602Notes

Reaction equation

HRID 1854602 reaction equation
ClC1C=CC(NC2C=C[CH:12]=[C:11]([C:15]3O[C:18]([C:20]4[CH:24]=[CH:23]SC=4)=[N:17][CH:16]=3)N=2)=NC=1.Cl[C:26]1[O:27][C:28]([C:31]2[N:36]=[C:35]([NH:37][C:38]3[CH:43]=[N:42][CH:41]=[CH:40][N:39]=3)[CH:34]=[CH:33][CH:32]=2)=[CH:29][N:30]=1.N1C2C(=CC(B(O)O)=CC=2)C=C1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.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>[NH:17]1[C:16]2[C:24](=[CH:23][C:12]([C:26]3[O:27][C:28]([C:31]4[N:36]=[C:35]([NH:37][C:38]5[CH:43]=[N:42][CH:41]=[CH:40][N:39]=5)[CH:34]=[CH:33][CH:32]=4)=[CH:29][N:30]=3)=[CH:11][CH:15]=2)[CH:20]=[CH:18]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27343615-Indolylboronic acidHCID 53312330HCID 53312330, compoundHCID 67324208HCID 67324208, compound

Product 1

HCID 67323295HCID 67323295, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Prepared as for (5-chloro-pyridin-2-yl)-[6-(2-thiophen-3-yl-oxazol-5-yl)-pyridin-2-yl]-amine from [6-(2-chloro-oxazol-5-yl)-pyridin-2-yl]-pyrazin-2-yl-amine, indole-5-boronic acid, Pd(PPh3)4 and K2CO3 in THF/water to afford the title compound as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ 11.37 (s, 1H), 10.08 (s, 1H), 9.28 (s, 1H), 8.38 (s, 1H), 8.30-8.25 (m, 1H), 8.16 (d, J=2.6 Hz, 1H), 7.93-7.81 (m, 2H), 7.79 (s, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.51-7.42 (m, 2H), 6.62 (s, 1H). (ESI+) m/z 338 (M+H)+. Retention time=1.81 mins (method 1).

Sources & evidence

ORD record
ord-dcbc36c4a80b4611863fb12a34c915b4
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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