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Water → 4-((3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)methyl)morpholine

HRID 633598
Notes
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Reaction equation

HRID 633598 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12]([C:13]3[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=3[O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[CH:11][N:10]([CH3:31])[C:5]2=[C:6]([O:8][CH3:9])[N:7]=1.[B-](F)(F)(F)[CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.[K+].C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:30][C:24]1[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=1[O:22][C:14]1[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:13]=1[C:12]1[C:4]2[C:5](=[C:6]([O:8][CH3:9])[N:7]=[C:2]([CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH:3]=2)[N:10]([CH3:31])[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 45588142Potassium trifluoro[(morpholin-4-yl)methyl]borate(1-)HCID 904161975-bromo-3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 904168824-((3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)methyl)morpholine
Yield 52.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of Example 182B (110 mg, 0.224 mmol), potassium trifluoro(morpholinomethyl)borate (55.7 mg, 0.269 mmol), palladium (II) acetate (3.02 mg, 0.013 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1′,1′-biphenyl]-2-yl)phosphine (12.83 mg, 0.027 mmol), and Cs2CO3 (219 mg, 0.673 mmol) in 4 mL dioxane-water (9:1) was heated under nitrogen in Biotage Initiator microwave oven at 150° C. for 45 minutes. Water was added, extracted with ethyl acetate (2×), washed with water (2×), saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, filtered. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel with a gradient of 0-8% methanol in dichloromethane to give the title compound (60 mg, 0.118 mmol, 52.4% yield).

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washwashed with water (2×), saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by column chromatography on silica gel with a gradient of 0-8% methanol in dichloromethane

Sources & evidence

ORD record
ord-a0791008b18b4bae99eb657d2c3e9157
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321764B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes