HCID 9930568, compound → Ammonia

HRID 367426Notes

Reaction equation

HRID 367426 reaction equation
[CH2:1](C([SnH3])=C(CCCC)CCCC)[CH2:2]CC.[C:16]([N:24]1[C:32]2[C:27](=[CH:28][C:29](Br)=[CH:30][CH:31]=2)[C:26]([C:34]2[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH:39]=2)=[CH:25]1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[NH3:24].[C:16]([N:24]1[C:32]2[C:27](=[CH:28][C:29]([CH:1]=[CH2:2])=[CH:30][CH:31]=2)[C:26]([C:34]2[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH:39]=2)=[CH:25]1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 9930568HCID 9930568, compoundHCID 21115800Tri(butyl)vinylstannane

Product 2

HCID 222AmmoniaYield 5%HCID 232881101-Benzoyl-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-vinylindole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Tributylvinylstannane was added to a solution of 1-benzoyl-5-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)indole (Example 6g) in DMF and the reaction mixture was heated to 100° C. overnight. The mixture was partitioned between ethyl acetate and water, sequentially washed with water and brine, and dried over sodium carbonate. Flash chromatography (silica gel, 5% 2M methanolic ammonia in dichloromethane) yielded 1-benzoyl-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-vinylindole.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washsequentially washed with water and brine
  3. dry with materialdried over sodium carbonate

Sources & evidence

ORD record
ord-6647f084409d4fdaa4a36b1138fb3644
Source dataset
uspto-grants-2000_10
Patent number
US06133287

Reaction notes

Loading…