2-Aminopyridine → HCID 68905611, compound

HRID 1986298Notes

Reaction equation

HRID 1986298 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[C:15]([Cl:16])=[CH:14][N:13]=[C:12]([NH:17][CH2:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)[N:11]=3)[S:7][C:6]=2[CH:28]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH2:35].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>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)C>[Cl:16][C:15]1[C:10]([C:8]2[S:7][C:6]3[CH:28]=[C:2]([NH:35][C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=4)[CH:3]=[CH:4][C:5]=3[CH:9]=2)=[N:11][C:12]([NH:17][CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 104392-AminopyridineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 68856796HCID 68856796, compound

Product 1

HCID 68905611HCID 68905611, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A microwave tube is charged with [4-(6-bromobenzo[b]thiophen-2-yl)-5-chloropyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine (45 mg, 0.094 mmol), 2.5 equivalent of pyridin-2-amine (28 mg, 0.30 mmol), 2 mol % of tris(dibenzylideneacetone)dipalladium(0) (1.7 mg, 0.0020 mmol), 6 mol % of Xantphos (3.5 mg, 0.0060 mmol), 2.5 equivalent of cesium carbonate (77 mg, 0.24 mmol) and acetonitrile (2 mL). The reaction is sealed and heated under microwave condition at 150° C. for 15 minutes, cooled down, filtered and then evaporated to furnish a red oil. The crude material is subjected to reverse phase purification, eluting with 10-70% CH3CN/0.01 M NH4HCO3 in water using a C18 Xterra column, to give the title compound as a pale yellow solid (15 mg, 33% yield). ES+(m/z) 494 (35Cl) and 496 (37Cl) [M+H].

Workup

  1. customThe reaction is sealed
  2. temperaturecooled down
  3. filtrationfiltered
  4. customevaporated
  5. customto furnish a red oil
  6. customphase purification
  7. washeluting with 10-70% CH3CN/0.01 M NH4HCO3 in water using a C18 Xterra column

Sources & evidence

ORD record
ord-e1e89e72385447ebb93c958f10f2831b
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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