Ethyl Acetate → HCID 18629228, compound

HRID 1066759Notes

Reaction equation

HRID 1066759 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2.Cl[C:14]1[C:19]2[N:20]=[N:21][N:22]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[C:18]=2[CH:17]=[C:16]([CH3:28])[N:15]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C(OCC)(=O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[C:6]2[C:10]=1[N:9]([C:14]1[C:19]3[N:20]=[N:21][N:22]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[C:18]=3[CH:17]=[C:16]([CH3:28])[N:15]=1)[CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 184528187-Bromo-5-methoxyindolineHCID 186292554-chloro-1-[1-ethylpropyl]-6-methyl-1H-1,2,3-triazolo(4,5-c]pyridine

Product 1

HCID 18629228HCID 18629228, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 7-bromo-5-methoxyindoline (382 mg) and 4-chloro-1-[1-ethylpropyl]-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine (400 mg) in THF (2.0 mL) was added sodium bis(trimethylsilyl)amide (1.0 M in THF, 15 mL) at 0° C. The reaction was warmed to ambient temperature and stirred for 1 hour. Ethyl acetate (150 mL) was added and washed with water and brine. The organics were dried over MgSO4 and concentrated. The crude product was chromatographed on silica gel using ethyl acetate/hexane (1:4) as eluent to give 4-(7-bromo-5-methoxy-2,3-dihydro-1H-indol-1-yl)-1-(1-ethylpropyl]-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine (538 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-1594427271644410a74b30b91b0cdc8d
Source dataset
uspto-grants-2001_06
Patent number
US06245769B1

Reaction notes

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