Potassium Carbonate → HCID 57819888, compound

HRID 657393Notes

Reaction equation

HRID 657393 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][NH:9][C:10](=[O:36])[CH2:11][C:12]([NH:14][CH2:15][C:16]2[C:17]([NH:29][CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[C:18]3[CH:26]=[N:25][N:24]([CH2:27][CH3:28])[C:19]3=[N:20][C:21]=2[CH2:22][CH3:23])=[O:13])[CH:5]=[CH:6][CH:7]=1.[CH:37]([C:39]1[CH:40]=[C:41](B(O)O)[CH:42]=[CH:43][CH:44]=1)=[O:38].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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]>[CH2:27]([N:24]1[C:19]2=[N:20][C:21]([CH2:22][CH3:23])=[C:16]([CH2:15][NH:14][C:12](=[O:13])[CH2:11][C:10]([NH:9][CH2:8][C:4]3[CH:3]=[C:2]([C:43]4[CH:42]=[CH:41][CH:40]=[C:39]([CH:37]=[O:38])[CH:44]=4)[CH:7]=[CH:6][CH:5]=3)=[O:36])[C:17]([NH:29][CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[C:18]2[CH:26]=[N:25]1)[CH3:28]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343563-Formylphenylboronic acidHCID 57819882HCID 57819882, compound

Product 1

HCID 57819888HCID 57819888, compoundYield 70.7%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

To N-[(3-bromophenyl)methyl]-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide (1.356 g, 2.432 mmol) was added (3-formylphenyl)boronic acid (0.401 g, 2.68 mmol) followed by K2CO3 (1.008 g, 7.30 mmol) and PdCl2(dppf) (0.071 g, 0.097 mmol) in 1,4-dioxane (14.95 mL) and water (4.98 mL). The mixture was heated under microwave for 15 min at 130° C. The solvent was removed by Glas-Col and DCM was added. The crude product was filtered through sintered glass funnel. Then the solid was washed with water and DCM to afford 1.0023 g (70.7%) of the title compound. LC-MS (M+H)+ 583.

Workup

  1. customThe solvent was removed by Glas-Col and DCM
  2. additionwas added
  3. filtrationThe crude product was filtered through sintered glass funnel
  4. washThen the solid was washed with water and DCM

Sources & evidence

ORD record
ord-2bfbf3cf24234cbb86a9743f351d5f01
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

Loading…