tert-Butyl N-(2-bromoethyl)carbamate → HCID 89827882, compound

HRID 1521491Notes

Reaction equation

HRID 1521491 reaction equation
[CH3:1][CH:2]([CH3:16])[C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([S:14][CH3:15])[CH:8]=2)=[O:4].Br[CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].[OH-].[Na+].O>[C:3]([C:5]1[N:6]([CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([S:14][CH3:15])[CH:8]=2)(=[O:4])[CH:2]([CH3:16])[CH3:1]

Participants

6

Reactant 2

HCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 89815985HCID 89815985, compound

Product 1

HCID 89827882HCID 89827882, compoundYield 20.7%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-methyl-1-(6-(methylthio)-1H-indol-2-yl)propan-1-one (600 mg, 2.57 mmol) and Bu4NBr (4.12 g, 12.85 mmol) in 9 N NaOH (10 mL, cooled) was added tert-butyl (2-bromoethyl)carbamate (2.87 g, 12.85 mmol). The reaction mixture was stirred at rt for 72 h. The mixture was diluted with water (20 mL) at 0° C., extracted with EtOAc (20 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated and purified by column chromatography on silica gel eluting with PE/EtOAc 10:1 to afford tert-butyl (2-(2-isobutyryl-6-(methylthio)-1H-indol-1-yl)ethyl)carbamate (200 mg, 20.66% yield) as a colorless oil. LC-MS MS (ESI) m/z 321.1 [M-56+H]+, 277.1 [M-100+H]+. 1H NMR (CDCl3 400 MHz): δ 7.57 (d, J=8.4 Hz, 1H), 7.38 (s, 1H), 7.29 (s, 1H), 7.10 (d, J=8.4 Hz, 1H), 4.80 (brs, 1H), 4.62 (t, J=6.4 Hz, 2H), 3.58-3.42 (m, 3H), 2.58 (s, 3H), 1.38 (s, 9H), 1.24 (d, J=6.8 Hz, 6H).

Workup

  1. extractionextracted with EtOAc (20 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography on silica gel eluting with PE/EtOAc 10:1

Sources & evidence

ORD record
ord-c352965b65824c5490233ee3c0b6ae7b
Source dataset
uspto-grants-2015_07
Patent number
US09073931B2

Reaction notes

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