Triethylamine → Tert-butyl 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

HRID 1853830Notes

Reaction equation

HRID 1853830 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([CH:23]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH3:24])=[CH:19][CH:18]=1.B(Br)(Br)Br.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(N(CC)CC)C>ClCCl.O>[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([CH:23]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH3:24])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25134Boron tribromideHCID 90495Di-tert-butyl dicarbonateHCID 67458078tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Product 1

HCID 67459021Tert-butyl 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (0.96 g, 2.1 mmol) in dichloromethane (15 mL) at 0° C. was added BBr3 (1.0 M in methylene chloride, 15 mL, 15 mmol) and the reaction was stirred at that temperature for 1 h and quenched by pouring onto water or ice-water. The precipitate was filtered and suspended in DMF (8 mL). Di-tert-butyl dicarbonate (0.85 g, 3.9 mmol) and triethylamine (1.1 mL, 7.8 mmol) were added and the mixture was stirred at rt for 2 h. Water was added and the precipitate was filtered and purified by column chromatography to afford the desired product as a solid: ESI MS m/z 437 [C24H24N2O4S+H]+.

Workup

  1. customquenched
  2. additionby pouring onto water or ice-water
  3. filtrationThe precipitate was filtered
  4. stirringthe mixture was stirred at rt for 2 h
  5. filtrationthe precipitate was filtered
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-6a2453ab887647b5a283aca98a0953a0
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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