Toluene → HCID 86623606, compound

HRID 2246707Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:18]3C=N[CH:21]=[N:22][CH:23]=3)[N:11]([CH2:24][C:25]([OH:27])=[O:26])[C:10]=2[CH3:28])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:34]1C=NC=C[N:35]=1)CCC.[C:48]1([CH3:54])[CH:53]=CC=C[CH:49]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:18]3[CH:23]=[N:22][CH:21]=[CH:34][N:35]=3)[N:11]([CH2:24][C:25]([O:27][C:48]([CH3:54])([CH3:53])[CH3:49])=[O:26])[C:10]=2[CH3:28])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the product from Example 3 part (ii) (0.4 g) in toluene (4 ml) was added 2-tributylstannylpyrazine (0.32 g) and tetrakis(triphenylphosphine)palladium (0) (0.1 g). The reaction mixture was heated to 80° C. for 18 hours. The mixture was adsorbed onto silica and purified using column chromatography (33% EtOAc/hexane as eluent) to give the sub-title compound (160 mg).

Workup

custompurified

Sources & evidence

ORD record: ord-c3035e895d0d4017b68cc38b70dc80dd
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687535B2

Reaction notes

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