Methyl Acrylate → HCID 178499682, compound

HRID 1520342Notes

Reaction equation

HRID 1520342 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[N:6]=[C:5]2[OH:18].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:38]([O:42][CH3:43])(=[O:41])[CH:39]=[CH2:40].CCN(C(C)C)C(C)C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[OH:18][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:40]=[CH:39][C:38]([O:42][CH3:43])=[O:41])[CH:3]=2)[N:8]=[C:7]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:6]=1

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 178517517HCID 178517517, compound

Product 1

HCID 178499682HCID 178499682, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-iodo-2-(pyridin-3-yl) quinazolin-4-ol (synthesized as described in Scheme 1 and 4, substituting 5-iodo-2-nitrobenzoic acid for 2-nitro-5-propoxy-benzoic acid) (3.00 g, 8.6 mmol, 1.0 eq.), Pd(OAc)2 (48 mg, 0.21 mmol, 0.025 eq.) and PPh3 (113 mg, 0.43 mmol, 0.05 eq.) in DMF (8 mL) was added methyl acrylate (3.22 g, 25.8 mmol, 3.0 eq.) and DIPEA (1.22 g, 9.46 mmol, 1.1 eq.) under Ar atmosphere. The mixture was stirred at 110° C. overnight. After cooling, the mixture was filtered and the solid was washed with ethyl acetate three times to afford 1.30 g of xxxvi-a as green solid (yield 49%). LCMS m/z=308.0 (M+1) (Method B) (retention time=1.41 min).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. washthe solid was washed with ethyl acetate three times

Sources & evidence

ORD record
ord-2fa2c089d9604857b540902ac096d94d
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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