Ammonium Chloride → HCID 91342956, compound

HRID 857406Notes

Reaction equation

HRID 857406 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[C:9]2[C:10]([C:29](=O)[C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)=[C:11]3[CH:20]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19][CH2:18][N:12]3[C:13]=2[CH:14]=[C:15]([F:17])[CH:16]=1.[NH4+].[Cl-]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:7][C:8]1[C:9]2[C:10]([C:29]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)=[CH2:1])=[C:11]3[CH:20]([CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:19][CH2:18][N:12]3[C:13]=2[CH:14]=[C:15]([F:17])[CH:16]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 91070571HCID 91070571, compound

Product 1

HCID 91342956HCID 91342956, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of methyltriphenylphosphonium bromide (536 mg, 1.5 mmol) in THF (7 mL) at r.t. was added potassium tert-butoxide (1.5 mL, 1M THF solution). The mixture was stirred for 30 minutes at r.t. and a solution of the compound of Step 1 (190 mg, 0.38 mmol) in THF (7 mL) was added. The reaction mixture was stirred at 60° C. for 2 h, cooled and poured into aqueous saturated NH4Cl. The phases were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 20% EtOAc/hexane to give 150 mg of the title compound.

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 2 h
  2. temperaturecooled
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-373cad2ea7c84cee80d00024a4d6e5c4
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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