5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → HCID 66623872, compound

HRID 1907355Notes

Reaction equation

HRID 1907355 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[O:3]1.[Br:17][CH2:18][C:19]([C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[CH:26][N:27]2[S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:32])=[O:31])=[CH:23][CH:22]=1)=O>C(O)C>[BrH:17].[C:33]1([S:30]([N:27]2[C:28]3[C:24](=[CH:23][CH:22]=[C:21]([C:19]4[N:15]=[C:12]5[CH:11]=[CH:10][C:9]([B:4]6[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]6)=[CH:14][N:13]5[CH:18]=4)[CH:29]=3)[CH:25]=[CH:26]2)(=[O:32])=[O:31])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 86651942HCID 86651942, compound

Product 1

HCID 66623872HCID 66623872, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.6 g of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylamine and 2.7 g of 2-bromo-1-[1-(phenylsulphonyl)indol-6-yl]ethanone are placed in 70 ml of ethanol and the mixture is refluxed for 20 h. A precipitate forms and is recovered by filtration, washed with diethyl ether and oven-dried under reduced pressure. 2.3 g of compound are obtained.

Workup

  1. temperaturethe mixture is refluxed for 20 h
  2. filtrationA precipitate forms and is recovered by filtration
  3. washwashed with diethyl ether
  4. customoven-dried under reduced pressure

Sources & evidence

ORD record
ord-642b9faaccd4461a9b2013a40469320b
Source dataset
uspto-grants-2013_12
Patent number
US08598166B2

Reaction notes

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