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1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-amine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 反応物 | Sodium t-butoxide | HCID 23676156 | — |
| 反応物 | N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamide | HCID 24857547 | — |
| 反応物 | 5,8-Dibromoimidazo[1,2-a]pyrazine | HCID 53485949 | — |
| 反応物 | 4-(4-Dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenylamine | HCID 59023094 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-amine | HCID 59023092 | 36.1% |
反応手順
In the same way as described for Compound 90, step 1, using 5,8-dibromoimidazo[1,2-a]pyrazine (116.9 mg, 0.422 mmol), 4-(4-dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenylamine (91.7 g, 0.422 mmol), NaOtBu (56.8 mg, 0.591 mmol), Pd2(dba)3 (15.5 mg, 0.0169 mmol), Xantphos (19.5 mg, 0.0337 mmol) and toluene (5 mL). The crude product is purified by Isolute FlashSilicaII cartridge chromatography eluting with 99:1 DCM/NH3 (7M in MeOH), followed by 97:3 DCM:NH3 (7M in MeOH). The title compound (63 mg, 36%) is isolated after a second column chromatography purification eluting with 97:3 DCM:NH3 (7M in MeOH).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08173656B2 |
| 出典データセット | uspto-grants-2012_05 |
| ORD ID | ord-b933f04f976e4947aeff683e4abe8972 |
| 出典メモ | uspto-grants-2012_05 |