Pyrrolidine → HCID 66589117, compound

HRID 1093234Notes

Reaction equation

HRID 1093234 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.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].[NH:82]1[CH2:86][CH2:85][CH2:84][CH2:83]1>C1(C)C=CC=CC=1>[CH2:28]([N:4]1[C:5]2=[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]([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]([N:82]2[CH2:86][CH2:85][CH2:84][CH2:83]2)=[N:3]1)[CH3:29]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 66588933HCID 66588933, compound

Product 1

HCID 66589117HCID 66589117, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 (2.0 mL) was added Pd(dba)3 (20 mg)(10 mol %), Binap (80 mg) (30 mol %), sodium tert butoxide (82 mg) and excess pyrrolidine. The mixture was purged under nitrogen for 5 minutes and then heated to 65 C overnight. Concentrated in vacuo to give an oil that was purified by silica gel chromatography (EtOAc/Hexanes) to afford 35 mg of the desired product as a yellow oil. MS m/z=450 (M+H)

Workup

  1. customThe mixture was purged under nitrogen for 5 minutes
  2. temperatureheated to 65 C overnight
  3. concentrationConcentrated in vacuo
  4. customto give an oil that
  5. customwas purified by silica gel chromatography (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-075f26faf94f45cca467898c6417d5a0
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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