Sodium hydride → HCID 56649449, compound

HRID 1466792Notes

Reaction equation

HRID 1466792 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1.[H-].[Na+].Br.Br[CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1>CN(C=O)C.C1COCC1>[Cl:20][C:16]1[CH:15]=[C:14]2[C:19]([C:11]([S:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:2])=[O:22])=[C:12]([CH3:21])[N:13]2[CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 66765016HCID 66765016, compound

Product 1

HCID 56649449HCID 56649449, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The recovered crude material, along with an additional portion of the starting material, 3-(6-chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.075 g, 0.23 mmol), were dissolved in DMF:THF (1:1, 4 mL) and the reaction was cooled to 0° C. Sodium hydride (60% dispersion in mineral oil, 0.95 mmol) was added and after five minutes 3-(bromomethyl)pyridine hydrobromide (0.57 mmol) was added and the ice bath was removed. After 10 minutes, LCMS of the reaction mixture indicated that the starting material was consumed and that the product was also hydrolyzed to from the methyl ester to the free acid in situ. Standard aqueous workup and purification by preparatory HPLC (10-100% ACN in H2O) afforded the title compound.

Workup

  1. customThe recovered crude material
  2. additionwas added
  3. customthe ice bath was removed
  4. customwas consumed and that the product
  5. customStandard aqueous workup and purification by preparatory HPLC (10-100% ACN in H2O)

Sources & evidence

ORD record
ord-ef2ced21a1ad4c8cad70e6238f6892f3
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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