Ethyl Acetate → 5-(2-Fluoro-6-methylbenzo[b]furan-5-yl)-pyrazine-2-ylamine

HRID 874674ノート

反応式

HRID 874674 の反応式
Br[C:2]1[C:3]([CH3:12])=[CH:4][C:5]2[O:9][C:8]([F:10])=[CH:7][C:6]=2[CH:11]=1.[NH2:13][C:14]1[CH:19]=[N:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][N:15]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(=O)OCC>C(#N)C.O1CCOCC1.O>[F:10][C:8]1[O:9][C:5]2[CH:4]=[C:3]([CH3:12])[C:2]([C:17]3[N:18]=[CH:19][C:14]([NH2:13])=[N:15][CH:16]=3)=[CH:11][C:6]=2[CH:7]=1

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 179989875-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amineHCID 584873945-Bromo-2-fluoro-6-methyl-benzofuran

生成物 1

HCID 584868455-(2-Fluoro-6-methylbenzo[b]furan-5-yl)-pyrazine-2-ylamine収率 25.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

A mixture of 5-bromo-2-fluoro-6-methyl-benzofuran (230) (0.3 mmol), 2-aminopyrazine-5-boronic acid pinacol ester (133 mg, 2 eq), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (42 mg, 10% mol) and K3PO4 (127 mg, 0.6 mmol) in 1 ml ACN, 1 ml dioxane, 0.5 ml H2O was bubbled with argon before heated at 85° C. for 2 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine. Org. phase was dried over Na2SO4, concentrated and then subjected to silica gel flash column chromatography (0-100% B, A: hexane; B: EA) to give 5-(2-fluoro-6-methylbenzo[b]furan-5-yl)-pyrazine-2-ylamine (234) (18.5 mg, purity>95%, yield: 25.4%) as yellow solid.

後処理

  1. customwas bubbled with argon
  2. temperatureAfter cooling down to r.t.
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialphase was dried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-1b9dae784b524f59b861ac93521072b8
出典データセット
uspto-grants-2015_03
特許番号
US08980629B2

反応ノート

読み込み中…