Potassium Carbonate → Tert-butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate

HRID 1818236Notes

Reaction equation

HRID 1818236 reaction equation
C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[Br:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:29][CH2:30][C:31]3[CH:45]=[CH:44][C:34]([CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:33][CH:32]=3)=[C:21]([N+:26]([O-])=O)[CH:22]=[N:23]2)=[CH:18][CH:17]=1>O.ClCCl.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-]>[NH2:26][C:21]1[CH:22]=[N:23][C:24]2[C:19]([C:20]=1[NH:29][CH2:30][C:31]1[CH:45]=[CH:44][C:34]([CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[CH:33][CH:32]=1)=[CH:18][CH:17]=[C:16]([Br:15])[CH:25]=2

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 21984421Tert-butyl {4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate

Product 1

HCID 21984367Tert-butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamateYield 100.5%

Reagents, catalysts & solvents 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideCatalystHCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl viologen dibromide (0.069 g, 0.18 mmol), potassium carbonate (12.76 g, 92 mmol) in water (55 mL), and sodium hydrosulfite (11.25 g, 65 mmol) in water (55 mL) were added sequentially to a solution of tert-butyl {4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate (9.0 g, 18.5 mmol) in dichloromethane (110 mL). The resulting biphasic mixture was stirred for 20 hours. The reaction was diluted with water (600 mL) and dichloromethane (500 mL). The layers were separated and the aqueous fraction was extracted with dichloromethane. The organic fractions were combined and washed sequentially with water and saturated aqueous sodium chloride. The organic fraction was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 8.5 g of tert-butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate as a yellow-brown amorphous solid.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous fraction was extracted with dichloromethane
  3. washwashed sequentially with water and saturated aqueous sodium chloride
  4. dry with materialThe organic fraction was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fff2982085c846f1a2b1bc334ce3200f
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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