Water → 5-(4-tert-Butylphenyl)-3-[(ethoxycarbonylmethylmethylamino)methyl]-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

HRID 420993Notes

Reaction equation

HRID 420993 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][NH:7][CH3:8])[CH3:3].[CH2:10]([O:12][C:13]([C:15]1[N:16]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH:43]([CH3:45])[CH3:44])=[CH:38][CH:37]=2)[C:17]2[C:22]([C:23]=1C=O)=[CH:21][C:20]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=1)=[CH:19][CH:18]=2)=[O:14])[CH3:11].[BH3-][C:47]#N.[Na+].O>CO.C(O)(=O)C>[CH2:10]([O:12][C:13]([C:15]1[N:16]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH:43]([CH3:45])[CH3:44])=[CH:38][CH:37]=2)[C:17]2[C:22]([C:23]=1[CH2:8][N:7]([CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:9])[CH3:47])=[CH:21][C:20]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:33])[CH3:34])=[CH:28][CH:27]=1)=[CH:19][CH:18]=2)=[O:14])[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 866288225-(4-tert-Butylphenyl)-3-formyl-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

Product 1

HCID 666577165-(4-tert-Butylphenyl)-3-[(ethoxycarbonylmethylmethylamino)methyl]-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

N-Methyl glycine ethyl ester hydrochloride (255 mg, 1.66 mmol) was added to a suspension of 5-(4-tert-butylphenyl)-3-formyl-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester (400 mg, 0.83 mmol; see step (c) above) in MeOH (20 mL) and the pH was adjusted to 6 by the addition of a few drops of glacial acetic acid. After 1 h at rt, NaCNBH3 (75 mg, 1.18 mmol) was added and the mixture was stirred at rt for 24 h, poured into H2O and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried (Na2SO4), concentrated and purified by chromatography to give the sub-title compound. Yield 400 mg (87%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-b13ab7cdfa7a40dc82c0afd399429086
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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