Ethanol → 4-(2,4-difluorophenoxy)-3-(7-methoxy-1-methyl-5-(morpholinomethyl)-1H-pyrrolo[2,3-c]pyridin-3-yl)aniline

HRID 633599Notes

Reaction equation

HRID 633599 reaction equation
[F:1][C:2]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[C:14]1[C:22]2[C:17](=[C:18]([O:30][CH3:31])[N:19]=[C:20]([CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:21]=2)[N:16]([CH3:32])[CH:15]=1.[Cl-].[NH4+].C(O)C.O>O1CCCC1.C(OCC)(=O)C.[Fe]>[F:1][C:2]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[C:14]1[C:22]2[C:17](=[C:18]([O:30][CH3:31])[N:19]=[C:20]([CH2:23][N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[CH:21]=2)[N:16]([CH3:32])[CH:15]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 904168824-((3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)methyl)morpholine

Product 1

HCID 904168454-(2,4-difluorophenoxy)-3-(7-methoxy-1-methyl-5-(morpholinomethyl)-1H-pyrrolo[2,3-c]pyridin-3-yl)anilineYield 99%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 182C (58 mg, 0.114 mmol), ammonium chloride (6.08 mg, 0.114 mmol), iron (50.8 mg, 0.909 mmol), in 4 mL tetrahydrofuran and 4 mL ethanol and 2 mL water was heated at reflux for 3 hours. The mixture was diluted with ethyl acetate, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrated was concentrated to give the title compound (54 mg, 0.112 mmol, 99% yield).

Workup

  1. temperatureat reflux for 3 hours
  2. washwashed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrated was concentrated

Sources & evidence

ORD record
ord-cfd4d6a9c0b340ffb5704a6765efdab5
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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