Cesium carbonate → HCID 58337625, compound

HRID 1887455Notes

Reaction equation

HRID 1887455 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4](I)[CH:3]=1.[NH2:12][C:13]1[CH:14]=[N:15][CH:16]=[N:17][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2590861-Fluoro-3-iodo-5-nitrobenzeneHCID 344373Pyrimidin-5-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 58337625HCID 58337625, compoundYield 93%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

1-fluoro-3-iodo-5-nitrobenzene (100 mg, 0.375 mmol, 1.00 eq), 5-aminopyrimidine (43 mg, 0.45 mmol, 1.2 eq, Cs2CO3 (171 mg, 0.525 mmol, 1.40 eq), Pd2(dba)3 (17 mg, 0.030 mmol, 0.080 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (26 mg, 0.045 mmol, 0.12 eq) and dioxane (0.8 mL) were added to a microwave vial. The vial was purged with argon, capped and heated at 100° C. for 18 h. After cooling the reaction was filtered over a plug of celite and the plug was washed with 5% MeOH/CH2Cl2. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 81 mg (93%) of the title compound as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ 9.23 (s, 1H), 8.84 (s, 1H), 8.72 (s, 2H), 7.68 (s, 1H), 7.53 (d, J=8.6 Hz, 1H), 7.36 (d, J=10.7 Hz, 1H); ES-MS [M+1]+: 235.1.

Workup

  1. customThe vial was purged with argon
  2. customcapped
  3. temperatureAfter cooling the reaction
  4. filtrationwas filtered over a plug of celite
  5. washthe plug was washed with 5% MeOH/CH2Cl2
  6. customThe solvents were removed in vacuo
  7. customthe crude mixture was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e23fd49b30304048b062fccf8db4baea
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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