Cesium carbonate → HCID 59708490, compound

HRID 1641362Notes

Reaction equation

HRID 1641362 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-7e922d56a24e4d10b508b516acaf7f98
Source dataset
uspto-grants-2012_02
Patent number
US08114878B2

Reaction notes

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