Sodium bis(trimethylsilyl)amide → HCID 59186076, compound

HRID 1671311Notes

Reaction equation

HRID 1671311 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[C:19]1[N:20]2[N:27]=[C:26]([CH3:28])[C:25]([C:29](=O)[CH2:30][CH2:31][CH3:32])=[C:21]2[O:22][C:23]=1[CH3:24]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[C:19]1[N:20]2[N:27]=[C:26]([CH3:28])[C:25]([C:29](=[CH2:1])[CH2:30][CH2:31][CH3:32])=[C:21]2[O:22][C:23]=1[CH3:24]

Participants

5

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 67212437HCID 67212437, compound

Product 1

HCID 59186076HCID 59186076, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyltriphenylphosphonium bromide (0.814 g, 2.278 mmol) in THF (8 ml) is added 1.0M NaHMDS (in THF) (2.278 ml, 2.278 mmol) generating a yellow reaction mixture. After stirring at RT for 10 minutes, 1-[3-(2,4-dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazol-7-yl]-butan-1-one (0.400 g, 1.139 mmol) is added and the reaction mixture is stirred at RT for 16 hours: a tan solution turning brown O/N. The reaction is quenched with ammonium chloride (sat. aq. 2 ml). The reaction mixture is partitioned between EtOAc (50 ml) and H2O (50 ml) and extracted with EtOAc (3×20 ml). The combined organic extracts are washed with brine (1×50 ml), dried Na2SO4, filtered and concentrated in vacuo. The resulting residue is purified via Flashmaster SiO2 150 ml/50 g column eluting with 12:1 Iso-hexane/EtOAc to yield the title compound as a white crystalline solid; MS: 349.08 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 7.77 (1H, d), 7.59 (1H, d), 7.51 (1H, dd), 4.94 (1H, d), 4.85 (1H, d), 2.30 (3H, t), 2.18 (3H, s), 2.14 (3H, s), 1.35 (2H, m), 0.79 (3H, t).

Workup

  1. stirringthe reaction mixture is stirred at RT for 16 hours
  2. customThe reaction is quenched with ammonium chloride (sat. aq. 2 ml)
  3. customThe reaction mixture is partitioned between EtOAc (50 ml) and H2O (50 ml)
  4. extractionextracted with EtOAc (3×20 ml)
  5. washThe combined organic extracts are washed with brine (1×50 ml), dried Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue is purified via Flashmaster SiO2 150 ml/50 g column
  9. washeluting with 12:1 Iso-hexane/EtOAc

Sources & evidence

ORD record
ord-a963ce948f4e49cd93944554b7435058
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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