Cesium carbonate → HCID 59708490, compound

HRID 1911064Notes

Reaction equation

HRID 1911064 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[S:23](=[O:24])[CH2:22][CH2:21][C:11]=3[N:12]=[C:13]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[N:14]=2)[CH:5]=[CH:6][CH:7]=1.Br[C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1.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+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[S:23](=[O:24])[CH2:22][CH2:21][C:11]=3[N:12]=[C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:26]4[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=4)[CH2:17][CH2:16]3)[N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 12162Benzonitrile, 4-bromo-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59708391HCID 59708391, compound

Product 1

HCID 59708490HCID 59708490, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Under an argon atmosphere 315 mg (3-fluoro-phenyl)-(5-oxo-2-piperazin-1-yl-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-4-yl)-amine, 165 mg 4-bromo-benzonitrile, 21 mg palladium(II)acetate, 80 mg Xantphos and 415 mg caesium carbonate are stirred in 2.50 ml degassed toluene for 24 hours at 80° C. After cooling the reaction mixture is extracted with ethyl acetate and saturated sodium chloride solution. The organic phase is dried and evaporated to dryness. The residue is purified by preparative HPLC (method A). 146 mg of the product (36%) are obtained. HPLC (method A):RT=3.83 min.

Workup

  1. customdegassed toluene for 24 hours at 80° C
  2. temperatureAfter cooling the reaction mixture
  3. extractionis extracted with ethyl acetate and saturated sodium chloride solution
  4. customThe organic phase is dried
  5. customevaporated to dryness
  6. customThe residue is purified by preparative HPLC (method A)

Sources & evidence

ORD record
ord-e1bb7253f508416c8f0bdfe9cee3d0fa
Source dataset
uspto-grants-2013_12
Patent number
US08604039B2

Reaction notes

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