Acetic Acid → [5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-thiophen-2-ylmethyl-amine

HRID 25501

Reaction equation

HRID 25501 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[F:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[F:18])[NH:14][C:13]([C:19]1[CH:20]=[CH:21][C:22]([O:26][CH3:27])=[C:23]([NH2:25])[CH:24]=1)=[CH:12]2.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[F:18])[NH:14][C:13]([C:19]1[CH:20]=[CH:21][C:22]([O:26][CH3:27])=[C:23]([NH:25][CH2:6][C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH:24]=1)=[CH:12]2

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 73642-ThiophenecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine

Product 1

HCID 9947557[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-thiophen-2-ylmethyl-amineYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Thiophenecarboxaldehyde (0.112 g, 1.0 mmol) was added to a stirred mixture of 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine (0.29 g, 1.06 mmol) in methylene chloride (125 mL), followed by acetic acid (0.1 g, 1.67 mmol). The resulting mixture was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.23 g, 1.09 mmol) was added in one portion, and the resulting homogeneous solution stirred at room temperature for 6 days. Saturated aqueous sodium bicarbonate solution (100 mL) was added and the mixture stirred for 2 hours. The mixture was shaken and the organic layer separated. The solvent was evaporated to give a brown gum. Recrystallization from methanol/water gave the product as a brown solid (120 mg), mp 190-192° C.

Workup

  1. stirringthe resulting homogeneous solution stirred at room temperature for 6 days
  2. stirringthe mixture stirred for 2 hours
  3. stirringThe mixture was shaken
  4. customthe organic layer separated
  5. customThe solvent was evaporated
  6. customto give a brown gum
  7. customRecrystallization from methanol/water

Sources & evidence

ORD record
ord-adbbe9c4bdb14caca4ed935cc7bb7baf
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Linked notes

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