Methyl iodide → benzyl 2,4-bis(benzyloxy)-6-(2-((tert-butoxycarbonyl)(methyl)amino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-5-methylnicotinate

HRID 1481795Notes

Reaction equation

HRID 1481795 reaction equation
[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:33]=[CH:32][C:31]3[N:30]4[CH2:34][CH:35]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:36][C:29]4=[CH:28][C:27]=3[CH:26]=2)[C:22]([CH3:45])=[C:21]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:57]>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:33]=[CH:32][C:31]3[N:30]4[CH2:34][CH:35]([N:37]([C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[CH3:57])[CH2:36][C:29]4=[CH:28][C:27]=3[CH:26]=2)[C:22]([CH3:45])=[C:21]([O:46][CH2:47][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71284342benzyl 2,4-bis(benzyloxy)-6-(2-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-5-methylnicotinate

Product 1

HCID 71284507benzyl 2,4-bis(benzyloxy)-6-(2-((tert-butoxycarbonyl)(methyl)amino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-5-methylnicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 412, Step 3 (130 mg, 0.18 mmol) was dissolved in DMF (1 mL). Sodium hydride (60% dispersion in mineral oil, 15 mg, 0.36 mmol) was added to the mixture. After 10 min of vigorous stirring at room temperature, iodomethane (35 μL, 0.54 mmol) was added to the mixture. The mixture was stirred an additional 10 min at room temperature, and then was quenched with the addition of aqueous saturated NH4Cl solution (5 mL). The mixture was extracted with CH2Cl2 (5 mL). The organic extracts were concentrated. The residue was 97% pure by UPLC analysis and used without further purification.

Workup

  1. stirringThe mixture was stirred an additional 10 min at room temperature
  2. customwas quenched with the addition of aqueous saturated NH4Cl solution (5 mL)
  3. extractionThe mixture was extracted with CH2Cl2 (5 mL)
  4. concentrationThe organic extracts were concentrated
  5. customused without further purification

Sources & evidence

ORD record
ord-5e35e03a37f94028a117c8ed07cbc158
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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