Water → HCID 86718011、化合物

HRID 1500473ノート

反応式

HRID 1500473 の反応式
Br[C:2]1[C:7]2[CH2:8][C@@H:9]([CH3:11])[O:10][C:6]=2[C:5]([NH2:12])=[CH:4][C:3]=1[CH3:13].[N:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][C@@H:9]1[CH2:8][C:7]2[C:2]([C:17]3[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=3)=[C:3]([CH3:13])[CH:4]=[C:5]([NH2:12])[C:6]=2[O:10]1

参加物

7

反応物 4

HCID 962Water2 回HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86718010HCID 86718010、化合物

生成物 1

HCID 86718011HCID 86718011、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
135 °C

実験手順

The mixture of (R)-4-bromo-2,5-dimethyl-2,3-dihydrobenzofuran-7-amine (3g) (1.0 g, 4.3 mmol), pyridin-4-ylboronic acid (1.08 g, 8.77 mmol), Cs2CO3 (3.56 g, 10.9 mmol), Pd(PPh3)4 (0.506 g, 0.438 mmol) and water (9 mL) in DMF (44 mL) was stirred at 135° C. under N2 for 1 h. It was cooled to ambient temperature, poured into water (50 mL), extracted with EtOAc (150 mL, washed with water, brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1 to 5:1 to 1:1) to give the title compound (3h) as a solid. MS-ESI (m/z): 241 (M+1)+.

後処理

  1. temperatureIt was cooled to ambient temperature
  2. extractionextracted with EtOAc (150 mL
  3. washwashed with water, brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1 to 5:1 to 1:1)

出典と根拠

ORDレコード
ord-94dbb8de730440d2aae66504afb3c61b
出典データセット
uspto-grants-2015_12
特許番号
US09206166B2

反応ノート

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