Water → HCID 59198440, compound

HRID 1896499Notes

Reaction equation

HRID 1896499 reaction equation
Br[C:2]1[C:3]2[S:20][C:19]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=3[C:4]=2[C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.O.[CH3:27][N:28](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:25][C:23]1[CH:22]=[CH:21][C:19]2[S:20][C:3]3[C:2]([C:27]#[N:28])=[CH:7][N:6]=[C:5]([NH:8][CH2:9][C:10]4[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=4)[C:4]=3[C:18]=2[CH:24]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 59198473HCID 59198473, compound

Product 1

HCID 59198440HCID 59198440, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture containing 4-bromo-8-chloro-N-(4-methoxybenzyl)[1]benzothieno[3,2-c]pyridine-1-amine, Zn(CN)2 (1.2 equiv) and Pd(Ph3P)4 (0.1 equiv) in DMF (0.1 M) was placed in microwave reactor at 150° C. for 10 min. The reaction was poured into H2O, filtered and washed with MeOH.

Workup

  1. filtrationfiltered
  2. washwashed with MeOH

Sources & evidence

ORD record
ord-f27752931ec442e1be01fedae4d5b320
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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