Potassium Carbonate → HCID 53312330, compound

HRID 1854601Notes

Reaction equation

HRID 1854601 reaction equation
Cl[C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.[S:21]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22]1.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>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:4]3[O:3][C:2]([C:23]4[CH:24]=[CH:25][S:21][CH:22]=4)=[N:6][CH:5]=3)[N:12]=2)=[N:15][CH:16]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 67324626HCID 67324626, compound

Product 1

HCID 53312330HCID 53312330, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of [6-(2-chloro-oxazol-5-yl)-pyridin-2-yl]-(5-chloro-pyridin-2-yl)-amine (50 mg, 0.162 mmol) in THF (4 ml) and water (2 ml) was treated with 3-thiopheneboronic acid (25 mg, 0.195 mmol), Pd(PPh3)4 (19 mg, 0.0162 mmol) and K2CO3 (50 mg, 0.358 mmol) before heating to 100° C. for 60 h. The cooled mixture was treated with water and extracted with DCM. The combined organics were dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on SiO2, eluting with 1% EtOH in DCM to afford the title compound as an off-white solid (51 mg, 89%). 1H NMR (400 MHz, DMSO-d6) δ 10.05 (s, 1H), 8.33-8.31 (m, 1H), 8.28 (d, J=2.5 Hz, 1H), 8.15 (d, J=9.0 Hz, 1H), 7.89 (dd, J=9.0, 2.7 Hz, 1H), 7.85 (s, 1H), 7.83-7.77 (m, 2H), 7.69-7.65 (m, 1H), 7.49 (d, J=8.3 Hz, 1H), 7.40 (d, J=7.4 Hz, 1H). (ESI+) m/z 355 (M+H)+. Retention time=4.28 mins (method 1).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure before purification by column chromatography on SiO2
  5. washeluting with 1% EtOH in DCM

Sources & evidence

ORD record
ord-b0ab1c26e3aa40b0b6d0052fb3ae0949
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

Loading…