Sodium Carbonate → 1-Amino-7-phenyl[1]benzothieno[3,2-c]pyridine-4-carboxamide

HRID 1896537Notes

Reaction equation

HRID 1896537 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]3[CH:14]=[CH:13][C:12](Br)=[CH:11][C:9]=3[S:10][C:6]=2[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:7]2[C:8]3[CH:14]=[CH:13][C:12]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:11][C:9]=3[S:10][C:6]=2[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 235819291-Amino-7-bromo[1]benzothieno[3,2-c]pyridine-4-carboxamide

Product 1

HCID 235819981-Amino-7-phenyl[1]benzothieno[3,2-c]pyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-amino-7-bromo[1]benzothieno[3,2-c]pyridine-4-carboxamide (Example 12, Step 10) in DMF (0.1 M) was added phenylboronic acid (1.5 equiv). The mixture was degassed for 5 min, and 1 M Na2CO3 (3 equiv) and PdCl2dppf (0.1 equiv) were added. It was heated is the microwave reactor at 120° C. for 10 min. The reaction mixture was partitioned between EtOAc and H2O. The organic phase was separated, dried over MgSO4, filtered, evaporated and purified by flash chromatography (EtOAc/MeOH) to provide the title compound.

Workup

  1. customThe mixture was degassed for 5 min
  2. temperatureIt was heated
  3. customat 120° C.
  4. customfor 10 min
  5. customThe reaction mixture was partitioned between EtOAc and H2O
  6. customThe organic phase was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. custompurified by flash chromatography (EtOAc/MeOH)

Sources & evidence

ORD record
ord-891c0468fc5e40d48eb749d2d12181c4
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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