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

HRID 453281Notes

Reaction equation

HRID 453281 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]

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 6342AcetonitrileSolvent

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-c14acaece79a40798d4c2b84c46bc1d2
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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