Water → HCID 66588946, compound

HRID 1093235Notes

Reaction equation

HRID 1093235 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=3)=[N:8][C:9]=2[N:11]2[CH2:17][CH:16]3[O:18][CH:13]([CH2:14][CH2:15]3)[CH2:12]2)[N:4]([CH2:28][CH3:29])[N:3]=1.C(=O)(O)[O-].[Na+].[N:35]1[CH:40]=[CH:39][CH:38]=[C:37](B(O)O)[CH:36]=1.O>C1(C)C=CC=CC=1.CCO.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>[CH2:28]([N:4]1[C:5]2=[N:6][C:7]([C:19]3[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=3)=[N:8][C:9]([N:11]3[CH2:12][CH:13]4[O:18][CH:16]([CH2:15][CH2:14]4)[CH2:17]3)=[C:10]2[C:2]([C:37]2[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=2)=[N:3]1)[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27343783-Pyridinylboronic acidHCID 66588933HCID 66588933, compound

Product 1

HCID 66588946HCID 66588946, compoundYield 104.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

To a solution of 3-bromo-1-ethyl-6-(4-nitrophenyl)-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (100 mg)(0.21 mmol) in toluene/EtOH (1:1) (2.0 mL) was added Pd(PPh3)4 (12 mg) (10 mol %), aqueous sodium bicarbonate solution (2.0 M) (0.135 mL) and 3-pyridine boronic acid (32 mg) (0.26 mmol). The reaction was heated in the microwave for 20 minutes at 140 C. The reaction was cooled and added water and then extracted three times with EtOAc. Organics were dried (MgSO4) and filtered off through a pad of Magnesol and concentrated in vacuo. to give a yellow oil 100 mg. MS m/z=458 (M+H)

Workup

  1. temperatureThe reaction was heated in the microwave for 20 minutes at 140 C
  2. temperatureThe reaction was cooled
  3. extractionextracted three times with EtOAc
  4. dry with materialOrganics were dried (MgSO4)
  5. filtrationfiltered off through a pad of Magnesol
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6059ae7cf978455b9b0721d01923d8cd
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

Loading…