Cesium carbonate → HCID 9864242, compound

HRID 1827744Notes

Reaction equation

HRID 1827744 reaction equation
Br[C:2]1[C:3]2[N:4]([C:9]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[Cl:21])=[C:10]([CH3:12])[CH:11]=2)[N:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:22]([CH:24]([NH2:27])[CH2:25][CH3:26])[CH3:23].C1(PC2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC.CCOC(C)=O.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].O>[Cl:21][C:14]1[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=1[C:9]1[N:4]2[N:5]=[C:6]([CH3:8])[CH:7]=[C:2]([NH:27][CH:24]([CH2:25][CH3:26])[CH2:22][CH3:23])[C:3]2=[CH:11][C:10]=1[CH3:12]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 120193-PentanamineHCID 70017DiphenylphosphineHCID 22064012HCID 22064012, compound

Product 1

HCID 9864242HCID 9864242, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-bromo-7-(2-chloro-4-methoxyphenyl)-2,6-dimethylpyrrolo[1,2-b]pyridazine (0.99 g, 2.70 mmol), 1-ethylpropylamine (0.63 mL, 0.47 g, 5.40 mmol), 5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen4-yl](diphenyl)phosphine (0.26 g, 0.40 mmol), Cs2CO3 (1.38 g, 4.20 mmol) and Pd2(dba)3 (0.13 g, 0.14 mmol) in DME (15.0 mL) was refluxed for 17 h. After cooling to room temperature, the mixture was diluted with EtOAc. Water was added and the mixture was separated. The aqueous solution was extracted with EtOAc (2×) and the combined EtOAc solutions was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to dryness, the residue was subjected to column chromatography (silica gel, 1/10 EtOAc/heptane) to give 0.88 g (87%) of light yellow oil as the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.36 (d, J=8.5 Hz, 1H), 7.09 (d, J=2.6 Hz, 1H), 6.95 (dd, J=8.5, 2.6 Hz, 1H), 6.29 (s, 1H), 5.54 (s, 1H), 4.16 (d, J=8.4 Hz, 1H), 3.88 (s, 3H), 3.47–3.43 (m, 1H), 2.31 (s, 3H), 2.21 (s, 3H), 1.78–1.66 (m, 2H), 1.64–1.54 (m, 2H), 1.00 (t, J=7.3 Hz, 6H); MS m/z 372.24 (M++H).

Workup

  1. temperaturewas refluxed for 17 h
  2. customthe mixture was separated
  3. extractionThe aqueous solution was extracted with EtOAc (2×)
  4. dry with materialthe combined EtOAc solutions was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-018a502a4c1244c6934db4d618ae3f73
Source dataset
uspto-grants-2006_06
Patent number
US07056920B2

Reaction notes

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