Cesium fluoride → 4-(6-Amino-5-(oxazolo[4,5-b]pyridin-2-yl)pyridin-3-yl)-2-methoxyphenol

HRID 908446ノート

反応式

HRID 908446 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][C:4]=1[OH:18].Br[C:20]1[CH:21]=[C:22]([C:27]2[O:28][C:29]3[C:30]([N:35]=2)=[N:31][CH:32]=[CH:33][CH:34]=3)[C:23]([NH2:26])=[N:24][CH:25]=1.[F-].[Cs+]>CO.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:26][C:23]1[N:24]=[CH:25][C:20]([C:7]2[CH:6]=[CH:5][C:4]([OH:18])=[C:3]([O:2][CH3:1])[CH:8]=2)=[CH:21][C:22]=1[C:27]1[O:28][C:29]2[C:30]([N:35]=1)=[N:31][CH:32]=[CH:33][CH:34]=2

参加物

6

反応物 3

HCID 25953Cesium fluorideHCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 673883775-Bromo-3-(oxazolo[4,5-b]pyridin-2-yl)pyridin-2-amine

生成物 1

HCID 673884864-(6-Amino-5-(oxazolo[4,5-b]pyridin-2-yl)pyridin-3-yl)-2-methoxyphenol収率 87.1%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 887Methanol溶媒

反応条件

温度
120 °C

実験手順

A mixture of 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (90 mg), 5-bromo-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine (100 mg), caesium fluoride (0.038 g) and bis(triphenylphosphine) palladium chloride (12.06 mg) were suspended in methanol (2 ml) and sealed into a microwave tube. The reaction was degassed, purged with nitrogen and heated to 120° C. over a period of 20 minutes in the microwave reactor. The solvent was removed; the residue was diluted with water (20 ml) and stirred for 30 min. The mixture was filtered, washed with water (3×10 ml), dried; and washed with diethyl ether (4×15 ml) and dichloromethane/diethyl ether (10 ml) and dried overnight to give 4-(6-amino-5-(oxazolo[4,5-b]pyridin-2-yl)pyridin-3-yl)-2-methoxyphenol (100 mg); NMR Spectrum: (DMSOd6) 3.88 (s, 3H), 6.87 (d, 1H), 7.09 (dd, 1H), 7.24 (d, 1H), 7.48 (dd, 1H), 7.73 (bs, 2H), 8.25 (dd, 1H), 8.46 (d, 1H), 8.55 (dd, 1H), 8.60 (d, 1H), 9.09 (s, 1H); Mass spectrum: M+H+ 335.

後処理

  1. customsealed into a microwave tube
  2. customThe reaction was degassed
  3. custompurged with nitrogen
  4. customThe solvent was removed
  5. additionthe residue was diluted with water (20 ml)
  6. filtrationThe mixture was filtered
  7. washwashed with water (3×10 ml)
  8. customdried
  9. washand washed with diethyl ether (4×15 ml) and dichloromethane/diethyl ether (10 ml)
  10. customdried overnight

出典と根拠

ORDレコード
ord-5a40ce9592cf48fc906718064596300c
出典データセット
uspto-grants-2011_09
特許番号
US08017611B2

反応ノート

読み込み中…