Ammonium formate → HCID 67233024, compound

HRID 2368743Notes

Reaction equation

HRID 2368743 reaction equation
C([O-])=O.[NH4+].[CH2:5]([O:9][C:10]([C:12]1[N:17]=[C:16](Br)[C:15]2[CH:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[S:21][C:14]=2[C:13]=1[OH:29])=[O:11])[CH2:6][CH2:7][CH3:8].[CH2:30]([O:34][C:35]([C:37]1[C:38]([OH:54])=[C:39]2[CH:46]=[C:45]([C:47]3[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=3)[S:44][C:40]2=[C:41](Br)[N:42]=1)=[O:36])[CH2:31][CH2:32][CH3:33]>[Pd].C(OCC)(=O)C>[CH2:5]([O:9][C:10]([C:12]1[N:17]=[CH:16][C:15]2[CH:19]=[C:20]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[S:21][C:14]=2[C:13]=1[OH:29])=[O:11])[CH2:6][CH2:7][CH3:8].[CH2:30]([O:34][C:35]([C:37]1[C:38]([OH:54])=[C:39]2[CH:46]=[C:45]([C:47]3[CH:48]=[CH:49][C:50]([F:53])=[CH:51][CH:52]=3)[S:44][C:40]2=[CH:41][N:42]=1)=[O:36])[CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 3

HCID 2723923Ammonium formateHCID 86607514HCID 86607514, compoundHCID 86607515HCID 86607515, compound

Product 2

HCID 67233024HCID 67233024, compoundHCID 67233288HCID 67233288, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of palladium on carbon (10%, 20 mg), ammonium formate (74.4 mg, 1.18 mmol), 4-bromo-2-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid butyl ester and 7-bromo-2-(4-fluoro-phenyl)-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester (50 mg, 0.118 mmol), example 34-c, in ethyl acetate (1.5 mL) was refluxed for 2.5 h. The catalyst was filtered off and the resulting solution was concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-60% ethyl acetate in hexanes to produce 11.0 mg of 2-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid butyl ester and 10.0 mg of 2-(4-fluoro-phenyl)-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester. MS for 2-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid butyl ester: (+) m/z 346.0 (M+1). MS for 2-(4-fluoro-phenyl)-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester: (+) m/z 346.0 (M+1).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe resulting solution was concentrated
  3. customThe crude product was purified by flash chromatography
  4. washeluting from silica gel with a gradient of 0-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7a712ba0f07f400986061bf36717735c
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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