Water → HCID 86718003、化合物

HRID 1500464ノート

反応式

HRID 1500464 の反応式
Br[C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([NH2:11])=[CH:4][C:3]=1[CH3:12].[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=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>[CH3:12][C:3]1[CH:4]=[C:5]([NH2:11])[C:6]2[O:10][CH2:9][CH2:8][C:7]=2[C:2]=1[C:16]1[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=1

参加物

7

反応物 4

HCID 962Water2 回HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86718002HCID 86718002、化合物

生成物 1

HCID 86718003HCID 86718003、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

A mixture of 4-bromo-5-methyl-2,3-dihydrobenzofuran-7-amine (1e) (0.80 g, 3.5 mmol), pyridin-4-ylboronic acid (0.86 g, 7 mmol), Cs2CO3 (2.84 g, 8.7 mmol), Pd(PPh3)4 (0.40 g, 0.346 mmol) and water (7 mL) in DMF (35 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 (1f) as a yellow solid. MS-ESI (m/z): 227 (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-efc5e3350aa945acb5f09b467ebb132c
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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