Tetrahydrofuran → 6H-Pyrido[3a(2),2a(2):4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acid, 7,8,9,10-tetrahydro-6-oxo-, ethyl ester

HRID 1521701노트

반응식

HRID 1521701 반응식
[NH:1]1[C:5]2=[N:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:15]([O:17]CC)=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][N:30]1[Si](C)(C)CC[Si]1(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>CN1C(=O)CCC1>[O:17]=[C:15]1[NH:30][CH2:29][CH2:28][CH2:27][N:1]2[C:5]3[N:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=[CH:9][C:4]=3[CH:3]=[C:2]12

참가 물질

7

반응물 5

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 42924111-(3-Bromoprop-1-yl)-2,2,5,5-tetramethyl-1,2,5-azadisilolidineHCID 67236396Diethyl 1H-pyrrolo[2,3-B]pyridine-2,6-dicarboxylate2회

생성물 1

HCID 672367606H-Pyrido[3a(2),2a(2):4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acid, 7,8,9,10-tetrahydro-6-oxo-, ethyl ester수율 93.1%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a solution of diethyl 1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (Intermediate D, 2.00 g, 7.23 mmol) in NMP (20 mL) is added potassium carbonate (3.16 g, 22.9 mmol) and 1-(3-bromopropyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane (2.28 mL, 9.15 mmol). The mixture is stirred at room temperature for 16 h. 1M TBAF in THF (9.15 mL, 9.15 mmol) is added and the mixture is stirred at room temperature for 3 h. The reaction is poured over ice and the resulting solid is collected by filtration. The crude material is purified via trituration with CH2Cl2/diethyl ether to afford the title compound as a yellow solid (1.84 g, 88%). LCMS: 274.70 (M+H+).

후처리

  1. stirringthe mixture is stirred at room temperature for 3 h
  2. additionThe reaction is poured over ice
  3. filtrationthe resulting solid is collected by filtration
  4. customThe crude material is purified via trituration with CH2Cl2/diethyl ether

출처 및 근거

ORD 기록
ord-7ae0bb26a1f84273b81fffd3c25aeaaa
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073926B2

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