Water → HCID 67333492, compound

HRID 1170178Notes

Reaction equation

HRID 1170178 reaction equation
I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][C:14]1[O:15][C:16]([CH3:19])=[CH:17][CH:18]=1)=[N:7]2.O.[CH3:21][N:22](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:19][C:16]1[O:15][C:14]([CH2:13][NH:12][C:6]2[CH:5]=[CH:4][C:3]3[C:2]([C:21]#[N:22])=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 67334536HCID 67334536, compound

Product 1

HCID 67333492HCID 67333492, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
160 °C

Procedure

A stirred mixture of (5-iodo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine (example 50, step A) (500 mg, 1.37 mmol), zinc cyanide (177 mg, 1.5 mmol) and tetrakis-(triphenylphosphine)-palladium (159 mg, 0.14 mmol) in DMF (5 ml) was heated at 160° C. for 15 min in a microwave reactor. The reaction mixture was poured into water (15 ml) and extracted with ethyl acetate (2×10 ml). The combined organic layers were washed with brine (10 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel to yield 2-[(5-methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbonitrile as light brown solid (346 mg, 91%).

Workup

  1. extractionextracted with ethyl acetate (2×10 ml)
  2. washThe combined organic layers were washed with brine (10 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel

Sources & evidence

ORD record
ord-8a2c8ab83be24ac39a1fefcc6537d6d8
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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