Nitrogen → tert-Butyl 3-(chloromethyl)indoline-1-carboxylate

HRID 349610Notes

Reaction equation

HRID 349610 reaction equation
Br[C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH:6]=[CH:7][Cl:8].CC(N=NC(C#N)(C)C)(C#N)C.N#N.CCCC[SnH](CCCC)CCCC>C1(C)C=CC=CC=1>[C:12]([O:11][C:9]([N:4]1[C:3]2[C:16](=[CH:17][CH:18]=[CH:19][CH:2]=2)[CH:6]([CH2:7][Cl:8])[CH2:5]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 947NitrogenHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 724293342-Bromo-N-(tert-butyloxycarbonyl)-N-(3-chloro-2-propen-1-yl) aniline

Product 1

HCID 58805418tert-Butyl 3-(chloromethyl)indoline-1-carboxylateYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 3.3 (110 mg, 0.318 mmol) and AIBN (21 mg, 0.127 mmol) in dry toluene (10 ml) was degassed for 15 mins with N2 and then heated to 90° C. Bu3SnH (84 μl, 0.318 mmol) was added to the mixture in four portions over an hour and the resulting mixture was stirred at 90° C. for a further 2 h. The mixture was then concentrated and purified by flash chromatography (SiO2, 0–10% EtOAc in hexane) to afford 3.4 (50 mg, 59%) as a colourless oil.FAB MS: (NBA/NaI) 267, (M+H+, expected 267) 292 (M+Na+, expected 292).

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified by flash chromatography (SiO2, 0–10% EtOAc in hexane)

Sources & evidence

ORD record
ord-318d9f17868242d896b68064fd8083d3
Source dataset
uspto-grants-2007_02
Patent number
US07179921B2

Reaction notes

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