6-Methoxy-3-pyridinylamine → HCID 59263506, compound

HRID 425657Notes

Reaction equation

HRID 425657 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1([C:20]3=[CH:21][C:22]4[O:26][CH2:25][O:24][C:23]=4[CH:27]=[C:19]3[O:18][CH2:17]1)[C:5](=[O:16])[N:6]2[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[NH2:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[N:33][CH:34]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C[O-].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:36][O:35][C:32]1[N:33]=[CH:34][C:29]([NH:28][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[C:4]2([C:20]4=[CH:21][C:22]5[O:26][CH2:25][O:24][C:23]=5[CH:27]=[C:19]4[O:18][CH2:17]2)[C:5](=[O:16])[N:6]3[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 811216-Methoxy-3-pyridinylamineHCID 634876Binap, (A+-)-HCID 10942334Sodium MethoxideHCID 592633394'-bromo-1'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)one

Product 1

HCID 59263506HCID 59263506, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

To an oven-dried 2-neck 25 mL round bottom flask equipped with a condenser was charged with 4′-bromo-1′-pentylspiro-(6,7-dihydrofuro-[2,3-f][1,3]benzodioxole-7,3′-indole)-2′-(1′H)-one (50.5 mg, 0.12 mmol), 5-amino-2-methoxypyridine (22.3 mg, 0.18 mmol), Pd2(dba)3 (10 mole %), BINAP (10 mole %) and sodium methoxide (12.9 mg, 0.24 mmol). The flask was flushed with nitrogen for 5 min followed by the addition of degassed toluene (5.00 mL). The reaction mixture was heated at reflux for 16 h. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate (20.0 mL) and washed with saturated ammonium chloride (10.0 mL), brine (10.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The brown residue was subjected to column chromatography eluting with ethyl acetate-hexane (20% to 50%) to yield the title compound (30.0 mg) in 54% yield: MS (ES+), m/z 474.3 (M+1).

Workup

  1. customTo an oven-dried 2-neck 25 mL round bottom flask equipped with a condenser
  2. customThe flask was flushed with nitrogen for 5 min
  3. additionfollowed by the addition of degassed toluene (5.00 mL)
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 16 h
  6. additionthe reaction mixture was diluted with ethyl acetate (20.0 mL)
  7. washwashed with saturated ammonium chloride (10.0 mL), brine (10.0 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo to dryness
  11. washeluting with ethyl acetate-hexane (20% to 50%)

Sources & evidence

ORD record
ord-08e976e1f20d4920b5637e644385e684
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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