Cesium carbonate → 3-(5,6-Dimethyl-3-thia-1,4,7,8a-tetraaza-as-indacen-8-yl)-benzamide

HRID 1051434Notes

Reaction equation

HRID 1051434 reaction equation
Br[C:2]1[N:13]2[C:5]([C:6]([CH3:14])=[N:7][C:8]3[S:9][CH:10]=[N:11][C:12]=32)=[C:4]([CH3:15])[N:3]=1.[C:16]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)(=[O:18])[NH2:17].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:14][C:6]1[C:5]2[N:13]([C:2]([C:23]3[CH:24]=[C:19]([CH:20]=[CH:21][CH:22]=3)[C:16]([NH2:17])=[O:18])=[N:3][C:4]=2[CH3:15])[C:12]2[N:11]=[CH:10][S:9][C:8]=2[N:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2737814(3-Carbamoylphenyl)boronic acidHCID 734258598-Bromo-5,6-dimethyl-3-thia-1,4,7,8a-tetraaza-as-indacene

Product 1

HCID 734259743-(5,6-Dimethyl-3-thia-1,4,7,8a-tetraaza-as-indacen-8-yl)-benzamideYield 53%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under argon atmosphere, a 5 mL microwave reaction vial was charged with 8-bromo-5,6-dimethyl-3-thia-1,4,7,8a-tetraaza-as-indacene from example 7 (10 mg, 0.035 mmol), 3-carbamoylphenylboronic acid (9 mg, 0.053 mmol) and Cs2CO3 (23 mg, 0.071 mmol) in DMF (3 mL) followed by the addition of Pd(dppf)Cl2 (3 mg, 3.5 μmol). The resulting suspension was heated on microwave at 100° C. for 1 hr. The reaction mixture was filtered and the filtrate was purified by Prep-HPLC to give the title compound (6 mg, yield: 52%) as a white solid.

Workup

  1. customUnder argon atmosphere, a 5 mL microwave reaction
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was purified by Prep-HPLC

Sources & evidence

ORD record
ord-1d18d74036eb4d70b41da0130aad473a
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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