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Benzyl 1-methyl-1H-indole-6carboxylate → 2-(1,3-Benzodioxol-5-yl)-2-[6-(benzyloxy)carbonyl-1-methyl-1h-indol-3-yl]acetic acid

HRID 322087
Notes
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Reaction equation

HRID 322087 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH:9]=2)[CH:4]=[CH:3]1.[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([CH:30](Br)[C:31]([OH:33])=[O:32])=[CH:29][C:24]=2[O:23][CH2:22]1>CN(C)C=O>[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([CH:30]([C:4]3[C:5]4[C:10](=[CH:9][C:8]([C:11]([O:13][CH2:14][C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)=[O:12])=[CH:7][CH:6]=4)[N:2]([CH3:1])[CH:3]=3)[C:31]([OH:33])=[O:32])=[CH:29][C:24]=2[O:23][CH2:22]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11265573Benzyl 1-methyl-1H-indole-6carboxylateHCID 113459502-(1,3-Benzodioxol-5-yl)-2-bromoacetic acid

Product 1

HCID 113741482-(1,3-Benzodioxol-5-yl)-2-[6-(benzyloxy)carbonyl-1-methyl-1h-indol-3-yl]acetic acidYield 60.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Benzyl 1-methyl-1H-indole-6-carboxylate (from (b), 9.8 g) and 2-(1,3-benzodioxol-5-yl)-2-bromoacetic acid (from Preparation 1, 10.5 g) were stirred together in dimethylformamide (100 ml) and a steady stream of nitrogen was passed through the solution which was warmed to 90° C. After 4 h the reaction mixture was cooled to room temperature and the dimethylformamide removed in vacuo. The oily residue was partitioned between ethyl acetate (300 ml) and 2M hydrochloric acid and the organic phase was washed with more 2M hydrochloric acid (3×50 ml) and brine (50 ml). The organic phase was dried (MgSO4) and decolourising charcoal was added. The slurry was filtered and concentrated to give an orange oil. Flash column chromatography (gradient elution from 100% CH2Cl2 to 95% CH2Cl2/5% MeOH) gave 9.97 g of the subtitle compound.

Workup

  1. temperatureAfter 4 h the reaction mixture was cooled to room temperature
  2. customthe dimethylformamide removed in vacuo
  3. customThe oily residue was partitioned between ethyl acetate (300 ml) and 2M hydrochloric acid
  4. washthe organic phase was washed with more 2M hydrochloric acid (3×50 ml) and brine (50 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. additionwas added
  7. filtrationThe slurry was filtered
  8. concentrationconcentrated
  9. customto give an orange oil
  10. washFlash column chromatography (gradient elution from 100% CH2Cl2 to 95% CH2Cl2/5% MeOH)

Sources & evidence

ORD record
ord-ccfc96d433df4499a3dab1e551c067e0
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211223B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes