Sodium Carbonate → HCID 22648055、化合物

HRID 394189ノート

反応式

HRID 394189 の反応式
Br[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:6](=[O:23])[N:7]2[C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22].C([O-])([O-])=O.[Na+].[Na+].[Cl:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1B(O)O.C(O)C.O>C1(C)C=CC=CC=1.C(OCC)(=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>[Cl:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:6](=[O:23])[N:7]2[C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 19096565Water ethanolHCID 226481455-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one

生成物 1

HCID 22648055HCID 22648055、化合物

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

1.07 g of 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one (1.99 mmol) were dissolved in 26 mL of toluene. Na2CO3 (1.26 g, 11.9 mmol), 2-chlorophenylboronic acid (934 mg, 5.97 mmol), and ethanol/water (6.4 mL:6.4 mL) were added under argon followed by Pd(Ph3P)4 (115 mg, 0.0995 mmol). The resulting reaction mixture was stirred at 100° C. for ca.4 h, cooled to rt, diluted with 150 mL of ethyl acetate, washed with 2×100 mL of saturated aqueous NaHCO3 and 100 mL of brine, dried over Na2SO4, and concentrated under reduced pressure. The product was purified by flash chromatography on Biotage 40M column, eluting with 80:20 hexanes-acetone to yield 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one. Mass spectrum (ESI) 568.1 (M+1).

後処理

  1. customThe resulting reaction mixture
  2. temperature4 h, cooled to rt
  3. washwashed with 2×100 mL of saturated aqueous NaHCO3 and 100 mL of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by flash chromatography on Biotage 40M column
  7. washeluting with 80:20 hexanes-acetone

出典と根拠

ORDレコード
ord-2f243b4285634dbbadef30547f79f833
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

反応ノート

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