Sodium bis(trimethylsilyl)amide → HCID 66823338, compound

HRID 1777195Notes

Reaction equation

HRID 1777195 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([OH:12])[C:4]=2[N+:3]=1[O-:13].[O:14]=[C:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:24]#[N:25])[CH:21]=2)[NH:16]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[C:24]([C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:14])[CH:23]2[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([OH:12])[C:4]=2[N+:3]=1[O-:13])#[N:25]

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileHCID 86663636HCID 86663636, compound

Product 1

HCID 66823338HCID 66823338, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared as described for Example 3.3 using 2-chloro-8-hydroxy-5,6,7,8-tetrahydroquinoline 1-oxide (100 mg, 0.501 mmol), 2-oxoindoline-5-carbonitrile (83 mg, 0.526 mmol), tetrahydrofuran (2.5 mL), and a 1.0 M solution of sodium bis(trimethylsilyl)amide (1.668 μL, 1.668 mmol). The reaction was quenched by addition of methanol (2.5 mL). The resulting solution was evaporated to dryness. The crude was used in the following reaction step without further purification.

Workup

  1. customThe reaction was quenched by addition of methanol (2.5 mL)
  2. customThe resulting solution was evaporated to dryness
  3. customThe crude was used in the following reaction step without further purification

Sources & evidence

ORD record
ord-6f22340f954146ebad3e5fdfd5a72d7d
Source dataset
uspto-grants-2016_02
Patent number
US09266855B2

Reaction notes

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