2-Methoxyaniline → HCID 57895141, compound

HRID 338588Notes

Reaction equation

HRID 338588 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:21]=[CH:20][C:19](I)=[CH:18][N:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:29][O:30][C:31]1[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=1[NH2:33].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.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].C(N(CC)CC)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:21]=[CH:20][C:19]([NH:33][C:32]5[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=5[O:30][CH3:29])=[CH:18][N:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

8

Reactant 4

HCID 70002-MethoxyanilineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57895170HCID 57895170, compound

Product 1

HCID 57895141HCID 57895141, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1-(Benzo[d][1,3]dioxol-5-yl)-N-(5-iodopyridin-2-yl)cyclopropanecarboxamide (816 mg, 0.200 mmol) was suspended in 1,4-dioxane (0.4 mL) and triethylamine (0.2 mL) containing cesium carbonate (91.2 mg, 0.0280 mmol), tris(dibenzylideneacetone)dipalladium (0) (1.8 mg, 0.0020 mmol), 2-methoxyaniline (0.027 mL, 0.24 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (XANTPHOS, 2.3 mg, 0.0040 mmol). The reaction mixture was heated to 100° C. for 15 hours. The crude product was then filtered, evaporated to dryness, dissolved in N,N-dimethylformamide (1 mL) and purified by reverse-phase preparative liquid chromatography utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoroacetic acid to yield the pure product (2.6 mg, 0.0049, 2.4%). ESI-MS m/z calc. 403.2. found 404.5 (M+1)+. Retention time 2.73 minutes.

Workup

  1. filtrationThe crude product was then filtered
  2. customevaporated to dryness
  3. dissolutiondissolved in N,N-dimethylformamide (1 mL)
  4. custompurified by reverse-phase preparative liquid chromatography
  5. customto yield the pure product (2.6 mg, 0.0049, 2.4%)

Sources & evidence

ORD record
ord-70ebe3577d4f4b468521485466a51d61
Source dataset
uspto-grants-2014_11
Patent number
US08889875B2

Reaction notes

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