Dimethylformamide → HCID 67288632, compound

HRID 46193Notes

Reaction equation

HRID 46193 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([CH2:8][C:9]2[CH:14]=[C:13]([C@H:15]3[C@H:20]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C@@H:19]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:18]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[O:16]3)[CH:12]=[CH:11][C:10]=2[Cl:54])=[CH:6][CH:7]=1.[CH3:55][N:56](C)C=O>[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>[Cl:54][C:10]1[CH:11]=[CH:12][C:13]([C@H:15]2[C@H:20]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C@@H:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:18]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[O:16]2)=[CH:14][C:9]=1[CH2:8][C:5]1[N:4]=[N:3][C:2]([C:55]#[N:56])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86664426HCID 86664426, compound

Product 1

HCID 67288632HCID 67288632, compoundYield 52%

Reagents, catalysts & solvents 2

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

Procedure

Intermediate 6 (compound 24, 4.0 g, 5.3 mmol) was added to a microwave reaction tube containing zinc cyanide (0.93 g, 7.9 mmol) and tetrakis(triphenylphosphine) palladium(0) (1.2 g, 1.1 mmol) in N,N-dimethylformamide (30 mL). The capped reaction tube was placed in a microwave reactor (Biotage® Initiator™) and the mixture was irradiated at 160° C. for 15 min. After dilution with ethyl acetate, the organic layer was subsequently washed with water, 10 wt % potassium carbonate and brine prior to drying over magnesium sulfate. After filtration and concentration under reduced pressure, the residue was purified on a Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes gradient) to yield the title compound (2.0 g, 2.7 mmol, 52%) as a white solid.

Workup

  1. customThe capped reaction tube
  2. customwas placed in a microwave reactor
  3. custom(Biotage® Initiator™) and the mixture was irradiated at 160° C. for 15 min
  4. washAfter dilution with ethyl acetate, the organic layer was subsequently washed with water, 10 wt % potassium carbonate and brine
  5. dry with materialto drying over magnesium sulfate
  6. filtrationAfter filtration and concentration under reduced pressure
  7. customthe residue was purified on a Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-f3cdcb4aa5744737b5a87fa20dec0d48
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

Loading…