Potassium Carbonate → HCID 24780799, compound

HRID 2241813Notes

Reaction equation

HRID 2241813 reaction equation
Br[C:2]1[O:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:17]3[CH:18]=[CH:19][C:14]([NH2:13])=[N:15][CH:16]=3)[O:3][C:4]=2[CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 68548730HCID 68548730, compound

Product 1

HCID 24780799HCID 24780799, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-6-methoxy-1,3-benzoxazole (0.877 mmol), 2-amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (1.3 mmol), K2CO3 2M aq. (3.5 mmol) and Pd(dppf)Cl2 (0.022 mmol) were mixed in DMF (5 ml) and stirred at 80° C. for 2 h. The solvents were evaporated under reduced pressure and the crude product was subjected to flash column chromatography followed by purification using reverse phase HPLC to afford the title compound as a white solid (68 mg). 1H NMR δ ppm 8.67 (br. s, 1H) 8.12-7.91 (m, 1H) 7.69-7.51 (m, 1H) 7.34 (br. s, 1H) 6.89-7.00 (m, 1H) 6.75 (br. s, 2H) 6.43-6.65 (m, 1H) 3.84 (s, 3H); MS m/z 242 (M+H).

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. customfollowed by purification

Sources & evidence

ORD record
ord-5861c2ece938468eb8787eb0c78469d6
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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