Acetonitrile → 1-Morpholino(4-(4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)phenyl)methanone

HRID 1046502Notes

Reaction equation

HRID 1046502 reaction equation
I[C:2]1[C:6]2[C:7]([O:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1.[N:37]1([C:43]([C:45]2[CH:50]=[CH:49][C:48](B(O)O)=[CH:47][CH:46]=2)=[O:44])[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.C(#N)C.C([O-])(=O)C.[K+]>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]>[O:40]1[CH2:41][CH2:42][N:37]([C:43]([C:45]2[CH:46]=[CH:47][C:48]([C:2]3[C:6]4[C:7]([O:11][CH:12]5[CH2:17][CH2:16][O:15][CH2:14][CH2:13]5)=[N:8][CH:9]=[CH:10][C:5]=4[N:4]([C:18]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:3]=3)=[CH:49][CH:50]=2)=[O:44])[CH2:38][CH2:39]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 517044Potassium AcetateHCID 2773546[4-(Morpholine-4-carbonyl)phenyl]boronic acidHCID 66826813HCID 66826813, compound

Product 1

HCID 668289671-Morpholino(4-(4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)phenyl)methanone

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

3-iodo-4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine (100 mg, 0.170 mmol), 4-(morpholine-4-carbonyl)phenylboronic acid (48 mg, 0.204 mmol), and 1,1′-bis(diphenylphosphino)ferrocenepalladium chloride (13.9 mg, 0.017 mmol) were charged in a microwave vial equipped with a stir bar. Acetonitrile (1.0 mL) and 1.0 M potassium acetate in water (0.41 mL) were then added, the reaction mixture was degassed with nitrogen for 5 min and then heated to 150° C. under microwave irradiation for 40 min. The crude mixture was filtered through Celite®, and concentrated to give the title compound.

Workup

  1. customvial equipped with a stir bar
  2. customthe reaction mixture was degassed with nitrogen for 5 min
  3. filtrationThe crude mixture was filtered through Celite®
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6210529ed0b3448ab6cc90d77be35921
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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