Tributylvinyltin → 9-Benzenesulfonyl-5-vinyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 1888506ノート

反応式

HRID 1888506 の反応式
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:27]#[N:28])=[C:18](OS(C(F)(F)F)(=O)=O)[C:13]=3[C:12]3[CH:29]=[CH:30][CH:31]=[N:32][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:33]([Sn](CCCC)(CCCC)C=C)[CH2:34]CC.[Cl-].[Li+]>O1CCOCC1.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>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:27]#[N:28])=[C:18]([CH:33]=[CH2:34])[C:13]=3[C:12]3[CH:29]=[CH:30][CH:31]=[N:32][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 58266643HCID 58266643、化合物

生成物 1

HCID 582665259-Benzenesulfonyl-5-vinyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile収率 53.7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of trifluoromethanesulfonic acid 9-benzenesulfonyl-6-cyano-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-5-yl ester (150 mg, 0.31 mmol), tributyl(vinyl)stannane (102 μL, 0.35 mmol), lithium chloride (40 mg, 0.93 mmol) and tetrakis(triphenylphosphine)palladium(0) (7.0 mg, 6.0 μmol) in dioxane (1.5 mL) was degassed with argon and heated under reflux for 18 h. The reaction mixture was allowed to cool to ambient temperature then diluted with DCM (9 mL) and methanol (1 mL). The resultant residue was purified by chromatography (silica, 2 g column, Si-SPE, 0-2% MeOH in DCM) and triturated with pentane (2×2 mL) to afford the title compound as a white solid (60 mg, 52%). LCMS (Method B): RT=3.73 min, M+H+=361.

後処理

  1. customwas degassed with argon
  2. temperatureheated
  3. temperatureunder reflux for 18 h
  4. additionthen diluted with DCM (9 mL) and methanol (1 mL)
  5. customThe resultant residue was purified by chromatography (silica, 2 g column, Si-SPE, 0-2% MeOH in DCM)
  6. customtriturated with pentane (2×2 mL)

出典と根拠

ORDレコード
ord-1690dfa08cae43748e2bd8271985576f
出典データセット
uspto-grants-2013_08
特許番号
US08501765B2

反応ノート

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