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 1521701ノート

反応式

HRID 1521701 の反応式
[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

参加物

7

反応物 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-dicarboxylate2 回

生成物 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 ester収率 93.1%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-7ae0bb26a1f84273b81fffd3c25aeaaa
出典データセット
uspto-grants-2015_07
特許番号
US09073926B2

反応ノート

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