Acetic Acid → N-((5-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)furan-2-yl)methyl)-2-methoxyethanamine

HRID 84374Notes

Reaction equation

HRID 84374 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[O:18][C:17](C=O)=[CH:16][CH:15]=3)[S:13][C:6]=12.[CH3:28][O:29][CH2:30][CH2:31][NH2:32].[BH-](OC(C)=O)(OC(C)=O)O[C:35](C)=O.[Na+].C(O)(=O)C>ClCCl>[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[O:18][C:17]([CH2:35][NH:32][CH2:31][CH2:30][O:29][CH3:28])=[CH:16][CH:15]=3)[S:13][C:6]=12

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866351855-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)furan-2-carbaldehyde

Product 1

HCID 67491421N-((5-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)furan-2-yl)methyl)-2-methoxyethanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 107 (2.00 g, 5.20 mmol), 2-methoxyethylamine (1.954 g, 26.02 mmol), NaBH(OAc)3 (5.52 g, 26.02 mmol) and acetic acid (1.49 ml, 26.02 mmol) in anhydrous dichloromethane was stirred at room temperature under nitrogen for five days. The reaction mixture was then carefully quenched with a saturated solution of NaHCO3 (pH 8-9), and extracted with DCM. The extract was dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound 108 as a yellow-orange sticky oil. The material was used in the next step without further purification. MS (m/z): 444.2 (M+H).

Workup

  1. customThe reaction mixture was then carefully quenched with a saturated solution of NaHCO3 (pH 8-9)
  2. extractionextracted with DCM
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-53bb44c193ff45c8a0df85892fadc318
Source dataset
uspto-grants-2014_09
Patent number
US08846927B2

Reaction notes

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