Hydrochloric Acid → HCID 58760777, compound

HRID 857343Notes

Reaction equation

HRID 857343 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)=[C:5]([C:20]([O:22]C)=O)[N:6]2[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].CC(C)([O-])C.[K+].Cl>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:24][C:25]1[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=1)=[C:5]1[C:20](=[O:22])[CH:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:12][N:6]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21867377HCID 21867377, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 58760777HCID 58760777, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of the indole of Step 2 (460 mg, 0.9 mmol) in THF (100 mL) at 0° C. was added potassium t-butoxide (1.2 mL of a 1M solution in THF The reaction mixture was stirred for 2 hours at 0° C. and 1N HCl was added. The phases were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to give 400 mg of a pale yellow solid used as such.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-92061330cc6a4fcab7d0813ace98c3c2
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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