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

HRID 1481796Notes

Reaction equation

HRID 1481796 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]([N:37](C(OC(C)(C)C)=O)[CH3:38])[CH2:36][C:29]4=[CH:28][C:27]=3[CH:26]=2)[C:22]([CH3:46])=[C:21]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=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>FC(F)(F)C(O)=O>[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][CH3:38])[CH2:36][C:29]4=[CH:28][C:27]=3[CH:26]=2)[C:22]([CH3:46])=[C:21]([O:47][CH2:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=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

3

Reactant 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

Product 1

HCID 71284780benzyl 2,4-bis(benzyloxy)-5-methyl-6-(2-(methylamino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)nicotinateYield 62.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The intermediate from Step 1 (˜0.18 mmol) was dissolved in trifluoroacetic acid (1 mL). After 1 min of stirring at room temperature, the mixture was partitioned in CH2Cl2 and aqueous 1 M K2CO3. The organic layer was removed, concentrated and chromatographed on silica gel (0-8% MeOH in CH2Cl2) to provide the product as a white powder (70 mg, 55%).

Workup

  1. customthe mixture was partitioned in CH2Cl2
  2. customThe organic layer was removed
  3. concentrationconcentrated
  4. customchromatographed on silica gel (0-8% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-b41abc08133f4a3d8171e45322a056f5
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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