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m-Formylbenzonitrile → [5-(5,6-Difluoro-1H-indol-2yl)-2-methoxy-phenyl]-(3-cyano-benzyl)-amine

HRID 25532
Notes
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Reaction equation

HRID 25532 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[F:21])[NH:17][C:16]([C:22]1[CH:23]=[CH:24][C:25]([O:29][CH3:30])=[C:26]([NH2:28])[CH:27]=1)=[CH:15]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)(=O)C>[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[F:21])[NH:17][C:16]([C:22]1[CH:23]=[CH:24][C:25]([O:29][CH3:30])=[C:26]([NH:28][CH2:6][C:5]3[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=3)[CH:27]=1)=[CH:15]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 90670m-FormylbenzonitrileHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine

Product 1

HCID 10293683[5-(5,6-Difluoro-1H-indol-2yl)-2-methoxy-phenyl]-(3-cyano-benzyl)-amineYield 64.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

3-Cyanobenzaldehyde (0.262 g, 2.0 mmol) was added to a stirred mixture of 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine (0.548 g, 2.0 mmol) in methylene chloride (125 mL), followed by acetic acid (0.2 g). The resulting mixture was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.46 g, 2.0 mmol) was added in one portion, and the resulting homogeneous solution stirred at room temperature for 3 days. Saturated aqueous sodium bicarbonate solution (100 mL) was added and the mixture stirred for 2 hours. The mixture was shaken, the organic layer separated and dried over Na2S4. The solvent was evaporated to give a white solid. Recrystallization from methanol gave the product (500 mg), mp 154-155° C.

Workup

  1. stirringthe resulting homogeneous solution stirred at room temperature for 3 days
  2. stirringthe mixture stirred for 2 hours
  3. stirringThe mixture was shaken
  4. customthe organic layer separated
  5. customdried over Na2S4
  6. customThe solvent was evaporated
  7. customto give a white solid
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-f64a7462a3de4a72833949b2f318e2f3
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858739B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes