Sodium Carbonate → methyl 3-(1-methylethyl)-7-nitro-1H-indole-5-carboxylate

HRID 852610

반응식

HRID 852610 반응식
Br[C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([N+:25]([O-:27])=[O:26])[C:12]=1[N:13]([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])C(=O)C(F)(F)F)[C:5]([O:7][CH2:8]C)=[O:6].C(O[Na])=O.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][CH:22]([C:21]1[C:2]2[C:12](=[C:11]([N+:25]([O-:27])=[O:26])[CH:10]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)[NH:13][CH:20]=1)[CH3:23]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 86602879Ethyl 3-bromo-4-[(3-methyl-2-buten-1-yl)(trifluoroacetyl)amino]-5-nitrobenzoateHCID 178526064HCID 178526064, 화합물

생성물 1

HCID 69358662methyl 3-(1-methylethyl)-7-nitro-1H-indole-5-carboxylate수율 135.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of ethyl 3-bromo-4-[(3-methyl-2-buten-1-yl)(trifluoroacetyl)amino]-5-nitrobenzoate (D215) (12.9 g, 28.5 mmol, 1 equiv) in DMF (130 ml) were added HCOONa (1.94 g, 28.5 mmol, 1 equiv), Na2CO3 (7.54 g, 71.2 mmol, 2.5 equiv), Bu4NCI (8.7 g, 31.3 mmol, 1.1 equiv) and palladium (II) acetate (320 mg, 1.42 mmol, 0.05 equiv) and the resulting mixture was stirred under nitrogen for 1 h then cooled to room temperature and concentrated in vacuo. The residue was partitioned between AcOEt and H2O and the two layers were separated. The insoluble material in the aqueous phase was filtered off through a pad of celite and the aqueous layer extracted twice with AcOEt. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo to give methyl 3-(1-methylethyl)-7-nitro-1H-indole-5-carboxylate (D218) (10.1 g, 128%) as a black solid which was used in the next step without further purification.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between AcOEt and H2O
  3. customthe two layers were separated
  4. filtrationThe insoluble material in the aqueous phase was filtered off through a pad of celite
  5. extractionthe aqueous layer extracted twice with AcOEt
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1296be22aad6463db62bdfedbffd8138
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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