Acetic Acid → 2-(6-(Pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)aniline

HRID 453282Notes

Reaction equation

HRID 453282 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[CH:14][N:13]=2)([O-])=O.C(O)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.[Fe]>[N:20]1([CH2:19][C:15]2[CH:16]=[C:17]3[N:18]=[C:10]([C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[NH2:1])[S:11][C:12]3=[N:13][CH:14]=2)[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 585518892-(2-Nitrophenyl)-6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridine

Product 1

HCID 585518882-(6-(Pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)anilineYield 98.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

Procedure

Iron powder (55 mmol, 3.1 g) was added to a solution of 2-(2-nitrophenyl)-6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridine (11.1 mmol, 3.8 g) in CH2Cl2 (100 mL) followed by acetic acid (10 mL). The reaction mixture was heated at reflux for 3 hours then cooled to room temperature. Na2CO3 (14 g) was added in portions. The mixture was passed through a pad of celite and rinsed with CH2Cl2. The combined filtrates were washed with Na2CO3 (3×20 mL), dried (MgSO4) and concentrated under reduced pressure to give 2-(6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)aniline (3.4 g, 98% yield) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. washrinsed with CH2Cl2
  4. washThe combined filtrates were washed with Na2CO3 (3×20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55b6df7d113e4e46b6100391b49f10ee
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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