Cesium carbonate → Ethyl 6-chloro-7-(4-(6-phenylpyrazin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate

HRID 1626443ノート

反応式

HRID 1626443 の反応式
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:15][O:16]3)=[CH:11][C:10]=2[Cl:24])=[CH:6][CH:5]=1)(=[O:3])[NH2:2].Cl[C:28]1[CH:33]=[N:32][CH:31]=[C:30]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCCC1>[Cl:24][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[O:8][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[NH:2][C:28]3[CH:33]=[N:32][CH:31]=[C:30]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:29]=3)=[CH:26][CH:25]=1)[O:16][CH2:15][CH2:14][CH:13]2[C:19]([O:21][CH2:22][CH3:23])=[O:20]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 52160922-Chloro-6-phenylpyrazineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67288619Ethyl 7-(4-carbamoylphenoxy)-6-chlorochroman-4-carboxylate

生成物 1

HCID 67289163Ethyl 6-chloro-7-(4-(6-phenylpyrazin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate収率 92.2%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

Argon was bubbled through a tetrahydrofuran (665 μl) solution of ethyl 7-(4-carbamoylphenoxy)-6-chlorochroman-4-carboxylate (50 mg, 0.133 mmol; Example 45, step A) and 2-chloro-6-phenylpyrazine (25.4 mg, 0.133 mmol) at ambient temperature in a vial. Cesium carbonate (47.7 mg, 0.146 mmol), XPHOS ligand (12.7 mg, 0.0266 mmol), and tris(dibenzylideneacetone)dipalladium (0) (6.09 mg, 0.0066 mmol) were added. Argon was bubbled through the reaction for two minutes and the vial was capped. The reaction was heated to 60° C. (oil bath temperature) for 18 hours. The reaction was cooled to ambient temperature and applied to silica gel. Elution with a gradient of ethyl acetate/hexanes (20 to 85%) provided the title compound (65 mg, 92%) as an off-white solid.

後処理

  1. customArgon was bubbled through the reaction for two minutes
  2. customthe vial was capped
  3. temperatureThe reaction was cooled to ambient temperature
  4. washElution with a gradient of ethyl acetate/hexanes (20 to 85%)

出典と根拠

ORDレコード
ord-b089c6e34de04948847d96fb534e2c4c
出典データセット
uspto-grants-2014_07
特許番号
US08785445B2

反応ノート

読み込み中…