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 1521701Notes

Reaction equation

HRID 1521701 reaction equation
[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

Participants

7

Reactant 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×

Product 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 esterYield 93.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-7ae0bb26a1f84273b81fffd3c25aeaaa
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

Loading…