Triphenylphosphine Oxide → morpholin-4-yl-[3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-methanone

HRID 2388917Notes

Reaction equation

HRID 2388917 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[N:11]1([C:17]([C:19]2[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=2)=[O:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(=O)(O)[O-].[Na+].C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(COC)OC.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.ClCCl>[N:11]1([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:2]3[CH:3]=[C:4]4[CH:10]=[N:9][NH:8][C:5]4=[N:6][CH:7]=3)[CH:20]=2)=[O:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 13097Triphenylphosphine OxideHCID 516892Sodium Bicarbonate2×HCID 36029163-(Morpholine-4-carbonyl)phenylboronic acidHCID 404274545-Bromopyrazolo[3,4-b]pyridine

Product 1

HCID 59836109morpholin-4-yl-[3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-methanoneYield 98.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-bromo-1H-pyrazolo[3,4-b]pyridine (1.50 g, 7.57 mmol), 3-(morpholin-4-carbonyl)phenylboronic acid (2.136 g, 9.09 mmol) and tetrakis(triphenylphosphine)palladium(0) (435 mL, 0.376 mmol) in dimethoxyethane (8 mL) and saturated aqueous solution of sodium bicarbonate (8 mL) was irradiated in a Personal Chemistry Optimizer at 175° C. for 60 min. The crude reaction mixture was distributed between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The aqueous phase was then extracted with dichloromethane, and then ethyl acetate and the combined organic phases were dried over sodium sulfate, filtered and concentrated to afford a pale green foam containing 80% of morpholin-4-yl-[3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-methanone (2.30 g, 80% yield) and 20% of triphenylphosphine oxide. 1H-NMR (500 MHz, d6-DMSO) δ13.75 (s, 1H), 8.87 (d, 1H), 8.54 (d, 1H), 8.21 (d, 1H), 7.85 (m, 1H), 7.77 (m, 1H), 7.58 (t, 1H), 7.41 (m, 1H).

Workup

  1. customwas irradiated in a Personal Chemistry Optimizer at 175° C. for 60 min
  2. customThe crude reaction mixture
  3. extractionThe aqueous phase was then extracted with dichloromethane
  4. dry with materialethyl acetate and the combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a pale green foam

Sources & evidence

ORD record
ord-50634a9ee7ec4097be21e193afe5f901
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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