4-Aminophenol → HCID 59398526, compound

HRID 2070015Notes

Reaction equation

HRID 2070015 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.CC(C)([O-])C.[K+].C(=O)([O-])[O-].[K+].[K+].[CH2:21]([O:28][CH2:29][N:30]1[C:34]2=[N:35][CH:36]=[CH:37][C:38](Cl)=[C:33]2[CH:32]=[CH:31]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN1C(=O)CCC1>[CH2:21]([O:28][CH2:29][N:30]1[C:34]2=[N:35][CH:36]=[CH:37][C:38]([O:8][C:3]3[CH:4]=[CH:5][C:6]([NH2:7])=[CH:1][CH:2]=3)=[C:33]2[CH:32]=[CH:31]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 11430Potassium CarbonateHCID 23665647Potassium tert-butoxideHCID 59398559HCID 59398559, compound

Product 1

HCID 59398526HCID 59398526, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

P-Aminophenol (8.4 g, 77 mmol) and potassium t-butoxide (14.4 g, 77 mmol) were dissolved in NMP (150 mL), and potassium carbonate (9 g, 39 mmol) was added thereto. The resulting mixture was stirred at room temperature for 1 hour, and an NMP (10 mL) solution of 1-benzyloxymethyl-4-chloro-1H-pyrrolo[2,3-b]pyridine (20 g, 73.3 mmol) was dropwise added thereto at 180° C. over 15 minutes. Subsequently, the mixture was stirred for 2 hours. The reaction container was cooled, and the content was poured on ice (650 g) and extracted with ethyl acetate (500 mL) three times. The combined organic layer was washed with saturated brine (150 mL) twice, dried, and concentrated. The residue was purified by silica-gel column chromatography (manufactured by Fuji Silysia, BW300, 7.5 cm×25 cm, n-hexane:EtOAc=1:1) to give 4-(1-benzyloxymethyl-1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline (21.9 g) as a light-yellow syrup (yield: 86%).

Workup

  1. waitat 180° C. over 15 minutes
  2. stirringSubsequently, the mixture was stirred for 2 hours
  3. temperatureThe reaction container was cooled
  4. additionthe content was poured on ice (650 g)
  5. extractionextracted with ethyl acetate (500 mL) three times
  6. washThe combined organic layer was washed with saturated brine (150 mL) twice
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by silica-gel column chromatography (manufactured by Fuji Silysia, BW300, 7.5 cm×25 cm, n-hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-9eb66073763d437faa8769e60ab29df9
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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