Pyrrolidine → (1-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

HRID 630548Notes

Reaction equation

HRID 630548 reaction equation
CN(C(ON1N=NC2[CH:12]=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.N1CCCC1.[Br:39][C:40]1[CH:41]=[N:42][C:43]([N:46]2[C:54]3[C:49](=[CH:50][CH:51]=[C:52]([C:55]([OH:57])=O)[CH:53]=3)[C:48]([S:58][CH3:59])=[CH:47]2)=[N:44][CH:45]=1>CN(C=O)C>[Br:39][C:40]1[CH:45]=[N:44][C:43]([N:46]2[C:54]3[C:49](=[CH:50][CH:51]=[C:52]([C:55]([N:15]4[CH2:14][CH2:13][CH2:12][CH2:10]4)=[O:57])[CH:53]=3)[C:48]([S:58][CH3:59])=[CH:47]2)=[N:42][CH:41]=1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1186660601-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid

Product 1

HCID 118676809(1-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (3.1 g, 8.24 mmol), diisopropylethylamine (3.6 ml, 20.6 mmol) and pyrrolidine (0.6 g, 8.24 mmol) were added to an ice cooled suspension of 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid (2.5 g, 6.86 mmol) in DMF (20 mL). The resulting mixture was stirred at room temperature for 16 h and then quenched with crushed ice. The precipitating solid was filtered off, washed with water and dissolved in dichloromethane. The organic phase was dried over sodium sulfate and evaporated. White solid. Yield: 2.1 g (73% of theory)

Workup

  1. temperaturecooled
  2. customquenched with crushed ice
  3. filtrationThe precipitating solid was filtered off
  4. washwashed with water
  5. dissolutiondissolved in dichloromethane
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-9c9513901e5442babc091de0322f68e3
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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