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Ammonium Chloride → HCID 86703313, compound

HRID 2409996
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Reaction equation

HRID 2409996 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32](OC)=[O:33])[N:27]=3)=[C:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:9]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:5][CH:4]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.O1CCCC1>[OH:33][CH2:32][C:28]1[N:27]=[C:26]([CH2:25][C:7]2[C:6]3[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[C:8]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:31]=[CH:30][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86703312HCID 86703312, compound

Product 1

HCID 86703313HCID 86703313, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 6-methoxy-3-(6-methoxycarbonylpyridin-2-ylmethyl)-2-phenyl-1H-indole-1-carboxylate (628 mg) in methanol/tetrahydrofuran (6 mL/6 mL) was added sodium borohydride (251 mg) under ice-cooling. The mixture was stirred under ice-cooling for 2 hours. To the reaction mixture was added a saturated aqueous ammonium chloride solution carefully, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain the title compound (593 mg). 1H-NMR (CDCl3) δ ppm: 1.23 (9H, s), 3.89 (3H, s), 3.95-4.01 (1H, m), 4.05 (2H, s), 4.65-4.72 (2H, m), 6.81-6.92 (2H, m), 6.94-7.00 (1H, m), 7.27-7.44 (6H, m), 7.44-7.52 (1H, m), 7.86 (1H, d, J=2.5 Hz).

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-60a95b4c5c1e406988946cf18040296c
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08815903B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes