Water → HCID 57500694, compound

HRID 1919677Notes

Reaction equation

HRID 1919677 reaction equation
Br[C:2]1[S:14][C:13]2[C:12]3[CH:11]=[CH:10][C:9]([C:15]#[N:16])=[CH:8][C:7]=3[N:6]=[C:5]([NH:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:4]=2[CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.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]>[CH3:21][N:20]([CH3:22])[CH2:19][CH2:18][NH:17][C:5]1[C:4]2[CH:3]=[C:2]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[S:14][C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([C:15]#[N:16])=[CH:8][C:7]=2[N:6]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 57500693HCID 57500693, compound

Product 1

HCID 57500694HCID 57500694, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

2-bromo-4-(2-(dimethylamino)ethylamino)thieno[3,2-c]quinoline-7-carbonitrile (1.0 eq, 55 mg, 0.146 mmol), benzene boronic acid (2.0 eq, 36 mg, 0.295 mmol), cesium carbonate (2.0 eq, 95 mg, 0.292 mmol) and PdCl2(dppf) (0.05 eq, 5 mg, 0.068 mmol) were mixed in dioxane (0.5 ml) containing 5% of water. The mixture was heated under microwave for 10 min at 120° C. After addition of water and filtration, 4-(2-(dimethylamino)ethylamino)-2-phenylthieno[3,2-c]quinoline-7-carbonitrile was isolated as a solid. LCMS (ES) m/z 373 [M+1]+.

Sources & evidence

ORD record
ord-bedb60dd79da4f7195cba51aef4197d1
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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