Sodium Carbonate → HCID 22648055, 화합물

HRID 394189노트

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HRID 394189 반응식
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]

참가 물질

8

반응물 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

생성물 1

HCID 22648055HCID 22648055, 화합물

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2f243b4285634dbbadef30547f79f833
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

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