Potassium Carbonate → 2-(1-benzothiophen-7-yl)-4-[1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl]furo[2,3-c]pyridin-7-amine

HRID 389498Notes

Reaction equation

HRID 389498 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH:12]=[C:11](B3OC(C)(C)C(C)(C)O3)[CH:10]=[N:9]2)[CH2:4][CH2:3]1.[S:22]1[C:26]2[C:27]([C:31]3[O:41][C:34]4=[C:35]([NH2:40])[N:36]=[CH:37][C:38](I)=[C:33]4[CH:32]=3)=[CH:28][CH:29]=[CH:30][C:25]=2[CH:24]=[CH:23]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[S:22]1[C:26]2[C:27]([C:31]3[O:41][C:34]4=[C:35]([NH2:40])[N:36]=[CH:37][C:38]([C:11]5[CH:10]=[N:9][N:8]([CH:5]6[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]6)[CH:12]=5)=[C:33]4[CH:32]=3)=[CH:28][CH:29]=[CH:30][C:25]=2[CH:24]=[CH:23]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 59231689(1-(1-Methylpiperidin-4-yl)-1H-pyrazol-4-yl)boronic acid pinacol esterHCID 667599752-(1-Benzothiophen-7-yl)-4-iodofuro[2,3-c]pyridin-7-amine

Product 1

HCID 667602582-(1-benzothiophen-7-yl)-4-[1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl]furo[2,3-c]pyridin-7-amineYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine (42.0 mg, 0.14 mmol) and 2-(1-benzothiophen-7-yl)-4-iodofuro[2,3-c]pyridin-7-amine (47.1 mg, 0.12 mmol) in 1,4-dioxane (0.81 mL) and H2O (0.2 mL) was charged with potassium carbonate (25 mg, 0.18 mmol) and (1,1′-bis(diphenylphosphino)ferrocene)palladium dichloride (0.9 mg, 0.01 mmol) under an atmosphere of nitrogen. The mixture was irradiated in a Biotage microwave reactor at 100° C. for 100 min. The reaction mixture was concentrated in vacuo to a solid. Purification by flash chromatography (0 to 10% 7 N NH3/MeOH:EtOAc afforded 17 mg (33%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 8.11 (d, J=7.58 Hz, 1H), 8.07 (s, 1H), 7.93 (d, J=8.08 Hz, 1H), 7.88 (d, J=7.07 Hz, 2H), 7.70 (d, J=5.31 Hz, 1H), 7.45-7.55 (m, 3H), 4.27 (dt, J=15.35, 7.86 Hz, 1H), 3.06 (d, J=11.62 Hz, 2H), 2.38 (s, 3H), 2.25-2.34 (m, 2H), 2.13-2.22 (m, 4H); MS (ESI): 431.17 [M+H]+; HPLC tR=0.90 min (TOF: polar—3 min).

Workup

  1. customThe mixture was irradiated in a Biotage microwave reactor at 100° C. for 100 min
  2. concentrationThe reaction mixture was concentrated in vacuo to a solid
  3. customPurification by flash chromatography (0 to 10% 7 N NH3/MeOH

Sources & evidence

ORD record
ord-4a6fd44d82e54ff292eae777b62cea38
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…