(4-Methoxyphenyl)boronic acid → Formic acid;7-(4-methoxyphenyl)-2-methyl-4-pyrrolidin-1-ylquinazoline

HRID 914929

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.[O:29]1CCOCC1.C(COC)OC>C(O)C.ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].ClCCl.[Pd+2]>[CH:20]([OH:19])=[O:29].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:11]=[C:10]3[C:5]([C:6]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)=[N:7][C:8]([CH3:12])=[N:9]3)=[CH:4][CH:3]=2)=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 44 mg (0.15 mmol) 7-Bromo-2-methyl-4-pyrrolidin-1-yl-quinazoline in 1.2 ml dioxane/dimethoxyethane 1:1 was added 57 mg (0.375 mmol) 4-methoxy-phenyl-boronic acid in 0.4 ml ethanol, 7 mg (0.007 mmol) Dichloro[1,1′-Bis(diphenylphosphino)-ferrocene]-palladium (II) dichloromethan adduct, and 0.6 ml 2 M Na2CO3aq. and the mixture was heated to 85° C. for 12 h. After filtration, the mixture was purified by reversed phase column chromatography eluting with an acetonitrile/water (formic acid) gradient yielding 17 mg (35%) of the title compound. MS m/e (%): 320.4 (M+H+, 100).

Workup

filtrationAfter filtration
customthe mixture was purified by reversed phase column chromatography
washeluting with an acetonitrile/water (formic acid) gradient

Sources & evidence

ORD record: ord-5832632b41374174addb484f008674ce
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265125B2

Linked notes

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