Water → HCID 178487698, compound

HRID 388690Notes

Reaction equation

HRID 388690 reaction equation
Br[C:2]1[N:3]=[C:4]([C:7]2[CH:16]=[C:15]([OH:17])[C:14]3[C:9](=[C:10]([Cl:20])[C:11]([O:18][CH3:19])=[CH:12][CH:13]=3)[N:8]=2)[S:5][CH:6]=1.O.C[C:23]([N:25](C)C)=O>[Zn].[C-]#N.[C-]#N.[Zn+2].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].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.[Fe+2]>[Cl:20][C:10]1[C:11]([O:18][CH3:19])=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[C:7]([C:4]1[S:5][CH:6]=[C:2]([C:23]#[N:25])[N:3]=1)[CH:16]=[C:15]2[OH:17]

Participants

8

Reactant 3

HCID 962WaterHCID 31374DimethylacetamideHCID 178487688HCID 178487688, compound

Product 1

HCID 178487698HCID 178487698, compoundYield 81%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The compound 262 (286 mg, 1 eq.) in degazed dimethylacetamide (10 mL), and Zn (4.5 mg, 0.09 eq.), Zn(CN)2 (84 mg, 0.6 eq.), Pd2 dba3 (21 mg, 0.03 eq.), and dppf (26 mg, 0.06 eq.) were heated at 110° C. under microwaves for 30 min. Then, water was added, the precipitate filtered and dissolved in ethyl acetate, dried, and concentrated under vacuum. The residue was purified by chromatography on a silica gel to give compound 263 as a yellow solid in 81% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 4.07 (s, 3H), 6.79 (br s, 1H), 7.08 (d, J=9.11 Hz, 1H), 8.19 (s, 1H), 8.28 (d, J=9.11 Hz, 1H), 9.74 (br s, 1H); MS (ESI, EI+): m/z=318.15 (MH+).

Workup

  1. filtrationthe precipitate filtered
  2. dissolutiondissolved in ethyl acetate
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by chromatography on a silica gel

Sources & evidence

ORD record
ord-6dec51ef251c4dcab50bd50ad2fbb788
Source dataset
uspto-grants-2013_02
Patent number
US08377962B2

Reaction notes

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