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

HRID 1896535Notes

Reaction equation

HRID 1896535 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.B(O)(O)[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=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:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=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 27343883-(Trifluoromethyl)phenylboronic acidHCID 235819291-Amino-7-bromo[1]benzothieno[3,2-c]pyridine-4-carboxamide

Product 1

HCID 235819951-Amino-7-[3-(trifluoromethyl)phenyl][1]benzothieno[3,2-c]pyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-amino7-bromo[1]benzothieno[3,2-c]pyridine-4-carboxamide (Example 12, Step 10), 3-trifluoromethylboronic acid (1.5 equiv), PdCl2dppf (0.1 equiv), Na2CO3 1 M (3.0 equiv) in DMF (0.15 M) was heated in the microwave reactor at 120° C. for 10 min. The reaction mixture was partitioned between EtOAc and H2O with the addition of DMSO. The organic phase was separated, dried over Na2SO4, filtered, evaporated and purified by flash chromatography (10% MeOH in CH2Cl2) to provide the title compound.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and H2O with the addition of DMSO
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by flash chromatography (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4c97769a30864db593db72011e5e4043
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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