Ammonium Chloride → HCID 15292265, compound

HRID 1648353Notes

Reaction equation

HRID 1648353 reaction equation
[CH3:1][Si:2]([CH3:22])([CH3:21])[CH2:3][CH2:4][O:5][C:6](=[O:20])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[NH:10][C:9]=1[CH3:19].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Cl:33][C:34]1[CH:42]=[C:41]([Cl:43])[CH:40]=[C:39]([Cl:44])[C:35]=1[C:36](Cl)=[O:37].[NH4+].[Cl-]>C1COCC1.C1(C)C=CC=CC=1.CN(P(N(C)C)(N(C)C)=O)C>[CH3:22][Si:2]([CH3:21])([CH3:1])[CH2:3][CH2:4][O:5][C:6](=[O:20])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]([C:36](=[O:37])[C:35]2[C:39]([Cl:44])=[CH:40][C:41]([Cl:43])=[CH:42][C:34]=2[Cl:33])[C:9]=1[CH3:19]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 15292264HCID 15292264, compound

Product 1

HCID 15292265HCID 15292265, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-78 °C

Procedure

To 5-methoxy-2-methyl-3-indolyl acetic acid 2-(trimethylsilyl)ethyl ester (2.00 g) in THF (20.0 mL) was added HMPA (2.0 mL). To the resulting mixture at -78° C. was added a 0.5M toluene solution of KHMDS (13.8 mL). After a period of 0.5 h, 2,4,6-trichlorobenzoyl chloride (1.03 mL) was added and the mixture was stirred 0.5 h at -78° C. then 0.5 h at 0° C. An aqueous solution of NH4Cl was then added and extracted with EtOAc. After purification by flash chromatography (10% EtOAc in hexane) the title compound was obtained (2.80 g) and used as such for the next step.

Workup

  1. custom0.5 h
  2. customat 0° C
  3. extractionextracted with EtOAc
  4. customAfter purification by flash chromatography (10% EtOAc in hexane) the title compound
  5. customwas obtained (2.80 g)

Sources & evidence

ORD record
ord-91ade6e8e69b45a5b50a15a0ae4e91e1
Source dataset
uspto-grants-1995_07
Patent number
US05436265

Reaction notes

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