Methyl iodide → 3-{[tert-Butoxycarbonyl-(4-morpholin-4-yl-phenyl)-amino]-methyl}-1-methyl-1H-indole-6-carboxylic acid methyl ester

HRID 416244Notes

Reaction equation

HRID 416244 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH2:14][N:15]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].[CH3:37]I>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH2:14][N:15]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)=[CH:18][CH:17]=3)=[CH:10][N:11]2[CH3:37])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 589305773-{[tert-Butoxycarbonyl-(4-morpholin-4-yl-phenyl)-amino]-methyl}1H-indole-6-carboxylic acid methyl ester

Product 1

HCID 589306133-{[tert-Butoxycarbonyl-(4-morpholin-4-yl-phenyl)-amino]-methyl}-1-methyl-1H-indole-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the ester 124 (473 mg, 1.02 mmol) in DMF (15 ml) was added 60% NaH (45 mg, 1.12 mmol). The solution was stirred for one hour at room temperature under nitrogen, cooled to 0° C., treated with MeI (170 μl, 1.12 mmol), warmed to room temperature and stirred overnight under nitrogen. The mixture was partitioned between water and AcOEt, organic layer was collected, dried over MgSO4 and concentrated in vacuo to yield 454 mg (93%). 1H-NMR (DMSO) δ: 7.99 (m, 1H), 7.56 (dd, J=1.4, 8.2 Hz, 1H); 7.47 (m, 1H); 7.27 (s, 1H); 6.86 (d, J=8.8 Hz, 2H); 6.75 (d, J=9.0 Hz, 2H); 4.86 (s, 2H); 3.83 (s, 3H); 3.76 (s, 3H); 3.67 (t, J=4.8 Hz, 4H); 3.01 (t, J=4.8 Hz, 4H); 1.37 (s, 9H).

Workup

  1. temperaturecooled to 0° C.
  2. temperaturewarmed to room temperature
  3. stirringstirred overnight under nitrogen
  4. customThe mixture was partitioned between water and AcOEt, organic layer
  5. customwas collected
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto yield 454 mg (93%)

Sources & evidence

ORD record
ord-c157fac7b7674b2eb8311c7a09675990
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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