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Water → 2-(2-Nitrophenyl)-6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridine

HRID 1799095
Notes
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Reaction equation

HRID 1799095 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:13][C:14]1[CH:15]=[C:16]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N+:29]([O-:31])=[O:30])[S:20][C:17]2=[N:18][CH:19]=1.O>CC#N>[N+:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:21]1[S:20][C:17]2[C:16]([N:22]=1)=[CH:15][C:14]([CH2:13][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:19][N:18]=2)([O-:31])=[O:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 585519076-(Chloromethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine

Product 1

HCID 585518892-(2-Nitrophenyl)-6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridineYield 84.7%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

Pyrrolidine (2.8 mol, 203 g) and K2CO3 (2.8 mol, 395 g) were added to a suspension of 6-(chloromethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine (0.52 mol, 175 g) in CH3CN (1.7 L). The reaction mixture was stirred at room temperature for 16 h. H2O (1 L) was added and the mixture stirred for 30 min. The CH3CN was removed under vacuum and the resulting mixture was extracted with CH2Cl2 (3×1.5 L). The combined organics were washed with brine, dried (Na2SO4) and concentrated under vacuum to give 2-(2-nitrophenyl)-6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridine as a dark oil (150 g, 76% yield).

Workup

  1. stirringthe mixture stirred for 30 min
  2. customThe CH3CN was removed under vacuum
  3. extractionthe resulting mixture was extracted with CH2Cl2 (3×1.5 L)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f93dc8cec0f446648cf28d8a155e4504
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08343997B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes