Dichloromethane → HCID 72207945, compound

HRID 1628301Notes

Reaction equation

HRID 1628301 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:5]2[CH:6]=[CH:7][NH:8][C:9]=2[CH:10]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C.C(Cl)[Cl:30]>>[ClH:30].[Br:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:5]2[CH2:6][CH2:7][NH:8][C:9]=2[CH:10]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 13770009methyl 6-bromo-1H-indole-4-carboxylate

Product 1

HCID 72207945HCID 72207945, compound

Procedure

To a 2000 ml flask were added of methyl 6-bromo-1H-indole-4-carboxylate 54.1.A (20.0 g, 78.7 mmole), 500 ml of DCM, 100 ml of TFA and triethylsilane (19 ml, 236 mmole). The reaction was stirred at room temperature for 16 hours at which time the reaction was partitioned between 1500 ml of DCM and 500 ml of saturated sodiumbicarbonate and the solvent was removed. The crude solid was resuspended in a 1 to 1 mixture 300 ml of EtAc/hexane and then HCl added (24 ml of 4N in Dioxane, 94.4 mmole), at which time the product crashed out. The solid was collected and dried to give of methyl 6-bromoindoline-4-carboxylate HCl 54.1.B as an off white solid (19.1 g, 85% yield).

Workup

  1. customwas partitioned between 1500 ml of DCM and 500 ml of saturated sodiumbicarbonate
  2. customthe solvent was removed
  3. additionHCl added (24 ml of 4N in Dioxane, 94.4 mmole)
  4. customThe solid was collected
  5. customdried

Sources & evidence

ORD record
ord-db6ae18895ec4b41b4131a1b3cdcd6f1
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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