Acetonitrile → HCID 58356419、化合物

HRID 244739

反応式

HRID 244739 の反応式
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[C:11]3[C:15]([CH:16]=[C:17](B4OC(C)(C)CC(C)(C)O4)[CH:18]=2)=[N:14][N:13](C2CCCCO2)[CH:12]=3)=[O:8])[N:6]=1.Br[C:36]1[CH:37]=[CH:38][C:39]2[O:43][CH:42]=[CH:41][C:40]=2[CH:44]=1.[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+].CC#N>O1CCOCC1.O.Cl[Pd]C1C=CC=CC=1C1C=CC=CC=1N(C)C.[C@H]12C[C@H](CC1)CC2PC1C[C@H]2C[C@@H]1CC2>[O:43]1[C:39]2[CH:38]=[CH:37][C:36]([C:17]3[CH:16]=[C:15]4[C:11]([CH:12]=[N:13][NH:14]4)=[C:10]([NH:9][C:7]([C:5]4[N:6]=[C:2]([CH3:1])[S:3][CH:4]=4)=[O:8])[CH:18]=3)=[CH:44][C:40]=2[CH:41]=[CH:42]1

参加物

8

反応物 4

HCID 6342AcetonitrileHCID 61695Pentapotassium TriphosphateHCID 90015Benzofuran, 5-bromo-HCID 58255833HCID 58255833、化合物

生成物 1

HCID 58356419HCID 58356419、化合物収率 10.7%

試薬・触媒・溶媒 3

HCID 178420574HCID 178420574、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

2-methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide (53 mg, 0.11 mmol) was dissolved in 1,4-Dioxane (0.4 mL) and added to 5-bromo-1-benzofuran (20 mg, 0.1 mmol, available from ABCR) in a microwave vessel. 1,4-Dioxane (0.4 ml) was added followed by chloro[2′-(dimethylamino)-2-biphenylyl]palladium-(1R,4S)-bicyclo[2.2.1]hept-2-yl[(1S,4R)-bicyclo[2.2.1]hept-2-yl]phosphane (1:1) (Solvias catalyst, 2 mg, 0.004 mmol, (heaped microspatula) available from ABCR) and a solution of potassium triphosphate (0.2 g, 0.1 mmol) in water (0.2 ml). The vessel was sealed and heated in CEM Discover using initial 150 W to 110° C. for 20 min. After cooling the solution was loaded onto a C18 SPE cartridge (pre-conditioned with MeCN/0.1% TFA) and flushed through with a further 3 ml MeCN/0.1% TFA. Solvent was removed by blowdown under a stream of nitrogen. The residue was dissolved in MeOH (0.51) and loaded onto a SCX-2 SPE cartridge (1 g) pre-conditioned with MeOH. The material was left on the column for 1 hr then eluted with 2M ammonia/MeOH and evaporated to dryness. The sample was purified by Mass Directed AutoPrep (Method C) to afford the title compound (4 mg).

後処理

  1. customThe vessel was sealed
  2. temperatureheated in CEM Discover
  3. customfor 20 min
  4. temperatureAfter cooling the solution
  5. customflushed through with a further 3 ml MeCN/0.1% TFA
  6. customSolvent was removed by blowdown under a stream of nitrogen
  7. dissolutionThe residue was dissolved in MeOH (0.51)
  8. washthen eluted with 2M ammonia/MeOH
  9. customevaporated to dryness
  10. customThe sample was purified by Mass Directed AutoPrep (Method C)

出典と根拠

ORDレコード
ord-32355e155b92499f906cc13497886f0f
出典データセット
uspto-grants-2014_02
特許番号
US08658635B2

関連ノート

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