Diethylamine → HCID 59198486, compound

HRID 1896528Notes

Reaction equation

HRID 1896528 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)=[N:10][CH:11]=[C:12]([C:15]#[N:16])[C:13]=3[S:14][C:4]=2[CH:3]=1.[CH3:27][S:28]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)(=[O:30])=[O:29].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(CC)CC>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][NH:17][C:9]2[C:8]3[C:5]4[CH:6]=[CH:7][C:2]([C:34]5[CH:35]=[CH:36][C:31]([S:28]([CH3:27])(=[O:30])=[O:29])=[CH:32][CH:33]=5)=[CH:3][C:4]=4[S:14][C:13]=3[C:12]([C:15]#[N:16])=[CH:11][N:10]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 591984657-Bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile

Product 1

HCID 59198486HCID 59198486, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
150 °C

Procedure

To a suspension of 7-bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile (Example 12, Step 9) and [4-(methylsulfonyl)phenyl]boronic acid (1.5 equiv) in 1-PrOH/H2O (4.5/1) (0.11 M) was added Pd2(dba)3 (0.03 equiv), Ph3P (0.06 equiv) and Et2NH (1.2 equiv). The mixture was degassed and heated to 150° C. for 10 min in a microwave reactor. The mixture was diluted with H2O and filtered. The crude product was swished with hot EtOH to give the title compound.

Workup

  1. customThe mixture was degassed
  2. additionThe mixture was diluted with H2O
  3. filtrationfiltered

Sources & evidence

ORD record
ord-3aa2590f909f4a43b8a4a97c867c20a8
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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