Potassium Phosphate, Tribasic → US10023592, Example 259

HRID 575744ノート

反応式

HRID 575744 の反応式
[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[C:5]2[CH:17]=[CH:18][O:19][C:4]=2[C:3]1=[O:20].[CH:21]1([CH2:24][O:25][C:26]2[C:27](I)=[N:28][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:30][CH:31]=2)[CH2:23][CH2:22]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:21]1([CH2:24][O:25][C:26]2[C:27]([C:6]3[C:5]4[CH:17]=[CH:18][O:19][C:4]=4[C:3](=[O:20])[N:2]([CH3:1])[CH:7]=3)=[N:28][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:30][CH:31]=2)[CH2:22][CH2:23]1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 1180225163-(Cyclopropylmethoxy)-2-iodo-6-methylsulfonylpyridineHCID 1240169906-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furo[2,3-c]pyridin-7-one

生成物 1

HCID 118021483US10023592, Example 259収率 62.3%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

A mixture of 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furo[2,3-c]pyridin-7-one (50 mg, 0.18 mmol), 3-(cyclopropylmethoxy)-2-iodo-6-methylsulfonylpyridine (53 mg, 0.15 mmol), K3PO4 (114 mg, 0.54 mmol), Pd(dppf)Cl2 (13 mg, 0.018 mmol) in dioxane (5 mL) was bubbled with nitrogen for 5 min and then stirred at 70° C. for 12 h. The reaction mixture was concentrated, treated with DCM (30 mL), washed with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by prep-HPLC to give the title compound (35 mg, yield: 52%) as an off-white solid.

後処理

  1. customwas bubbled with nitrogen for 5 min
  2. concentrationThe reaction mixture was concentrated
  3. additiontreated with DCM (30 mL)
  4. washwashed with water (30 mL) and brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by prep-HPLC

出典と根拠

ORDレコード
ord-bb88270f86ec4626a0d64e6820f4df77
出典データセット
uspto-grants-2015_05
特許番号
US09034900B2

反応ノート

読み込み中…