Acetic Acid → HCID 130473159, compound

HRID 2279929Notes

Reaction equation

HRID 2279929 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:31])[CH:5]=[C:6]([Cl:30])[C:7]=1[CH2:8][C@H:9]([O:20][C:21]([C:23]1[S:24][C:25]([CH:28]=O)=[CH:26][CH:27]=1)=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.[F:32][C:33]1[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=1[NH2:35].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[Cl:30][C:6]1[CH:5]=[N+:4]([O-:31])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@H:9]([O:20][C:21]([C:23]1[S:24][C:25]([CH2:28][NH:35][C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[F:32])=[CH:26][CH:27]=1)=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 95842-FluoroanilineHCID 5049666Sodium triacetoxyborohydrideHCID 118142901HCID 118142901, compound

Product 1

HCID 130473159HCID 130473159, compoundYield 32.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of [(1S)-2-(3,5-dichloro-1-oxidopyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]5-formylthiophene-2-carboxylate (128 mg, 0.265 mmol) in dichloromethane (5 mL) was added with 2-fluoroaniline (29 mg, 0.265 mmol) followed by glacial acetic acid (0.015 mL, 0.265 mmol). The reaction was stirred at room temperature for 6 h. Sodium triacetoxyborohydride (140 mg, 0.662 mmol) was added and the reaction was stirred at room temperature for 18 h. Water was added to quench the reaction and the organic layer was washed with brine, passed through a hydrophobic frit and the solvent was removed in vacuo. The crude material was purified by silica gel column chromatography, eluting with 0-100% EtOAc in DCM, to afford the title compound (50 mg, 32%) as a yellow oil.

Workup

  1. stirringthe reaction was stirred at room temperature for 18 h
  2. customto quench
  3. customthe reaction
  4. washthe organic layer was washed with brine
  5. customthe solvent was removed in vacuo
  6. customThe crude material was purified by silica gel column chromatography
  7. washeluting with 0-100% EtOAc in DCM

Sources & evidence

ORD record
ord-931f86a9a90d48288ab8214757fd1f92
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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