1,2-Dimethoxyethane → HCID 22396883, compound

HRID 1356339Notes

Reaction equation

HRID 1356339 reaction equation
Br[C:2]1[C:3]2[C:4]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11][C:5]=3[NH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1.[CH2:23](COC)OC.C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C.[CH3:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:23][C:43]1[CH:42]=[CH:41][CH:46]=[CH:45][C:44]=1[C:2]1[C:3]2[C:4]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:12][CH2:11][C:5]=3[NH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 21226206Ethyl acetate hexaneHCID 22396611HCID 22396611, compound

Product 1

HCID 22396883HCID 22396883, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

tert-Butyl 10-bromo-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (1.17 g, 3.2 mmol), Pd(PPh3)4 (0.39 g, 0.34 mmol), and dimethoxyethane (25 mL) were stirred at room temperature for 10 minutes then treated with 2-methylboronic acid (0.52 g, 3.8 mmol) and a 2 M solution of Na2CO3 (12 mL). The reaction was heated to reflux for 15.25 hours then cooled to room temperature and partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (2×) and the organic layers were combined, washed with brine, dried over MgSO4 and concentrated in vacuo to give a brown oil which was passed through a column of silica gel with 1:5 ethyl acetate/hexane to give 0.53 g (44%) of a brown oil as the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 15.25 hours
  3. custompartitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto give a brown oil which

Sources & evidence

ORD record
ord-6226e51b3a7d42bab44cb485c84000be
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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