Triethylamine → HCID 86628685, compound

HRID 2079911Notes

Reaction equation

HRID 2079911 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[C:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16]([F:22])[CH:15]=2)=[CH:5]1)([CH3:3])[CH3:2].C(N(CC)CC)C.[CH:30]([S:33](Cl)(=O)=[O:34])([CH3:32])[CH3:31]>C(Cl)Cl>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:6]2[C:7]3[C:12](=[CH:11][C:10]([NH:13][S:33]([CH:30]([CH3:32])[CH3:31])=[O:34])=[CH:9][CH:8]=3)[N:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)=[CH:15][C:16]=1[F:22])#[N:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 57442273HCID 57442273, compound

Product 1

HCID 86628685HCID 86628685, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Cool a mixture of 1-Isopropyl-3-(4-cyano-3-fluoro-phenyl)-1H-indol-6-ylamine (0.442 g, 1.51 mmol) and triethylamine (0.306 g, 3.02 mmol) in methylene chloride (10 mL) in a brine/ice bath under argon and treated with a solution of isopropyl sulfonyl chloride (0.210 g, 1.66 mmol) in methylene chloride and the resulting mixture was stirred in the cooling bath for 30 min. After this time dilute the reaction with methylene chloride (40 mL); wash with a saturated aqueous sodium bicarbonate solution (50 mL), then water (50 mL), then brine (50 mL); and dry over sodium sulfate. Remove the solids by filtration; concentrate the filtrate under reduced pressure. Triturate the residue with boiling methylene chloride (×3) then boiling acetonitrile to afford the title compound (0.212 g, 37%) as a white solid: mp 173-175° C. dec;

Workup

  1. temperatureCool
  2. additionAfter this time dilute
  3. washwash with a saturated aqueous sodium bicarbonate solution (50 mL)
  4. dry with materialand dry over sodium sulfate
  5. customRemove the solids
  6. filtrationby filtration
  7. concentrationconcentrate the filtrate under reduced pressure
  8. customTriturate the residue with boiling methylene chloride (×3)

Sources & evidence

ORD record
ord-02d827b5f4584644bd6b3560264cf842
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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