Triphenylphosphine → HCID 86606906, compound

HRID 2116771Notes

Reaction equation

HRID 2116771 reaction equation
BrBr.[N:3]1([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13](Br)[CH:12]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[C:40]([N:42](C)C)=O>[Zn].[C-]#N.[Zn+2].[C-]#N.[C].[Pd]>[N:3]1([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([C:40]#[N:42])[CH:12]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 24408Bromine2×HCID 31374DimethylacetamideHCID 86606907HCID 86606907, compound

Product 1

HCID 86606906HCID 86606906, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 178418390HCID 178418390, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

Zinc powder (78 mg, 1.2 mmol) is suspended into dimethylacetamide (5.7 mL), and thereto is added bromine (20 μl, 0.4 mmol) at room temperature under nitrogen. The mixture is stirred until the color of bromine disappears (15-25 ), and thereto are added 3-bromo-4-hydroxybenzoic acid (4-morpholinyl)amide (572 mg, 2 mmol), zinc cyanide (118 mg, 1.0 mmol), 5% palladium-carbon (170 mg, 0.08 mmol) and triphenylphosphine (84 mg, 0.32 mmol). The vacuum deaeration and the nitrogen introduction are repeated five times. The mixture is heated at 120° C. (internal temperature) for one hour, when the inversion rate is confirmed to be 99% by HPLC. After cooling to 25° C., the insoluble materials are separated by filtration to give 3-cyano-4-hydroxybenzoic acid (4-morpholinyl)amide. The yield is 453 mg (97.6%) when determined by HPLC.

Workup

  1. temperatureAfter cooling to 25° C.
  2. customthe insoluble materials are separated by filtration

Sources & evidence

ORD record
ord-455e868709f8450e84a9943d03daf273
Source dataset
uspto-grants-2008_10
Patent number
US07439368B2

Reaction notes

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