Benzophenone imine → HCID 86049192, compound

HRID 2235487Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([N:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[Na+].[C:21](=[NH:34])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:28]1([C:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[N:34][C:2]2[CH:7]=[C:6]([N:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][N:3]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 0.52 g (2.4 mmol) of 2-chloro-N4,N4-dipropylpyridin-4-amine, 0.076 g (0.12 mmol) of racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (BINAP), 0.33 g (3.4 mmol) of sodium tert-butoxide and 0.027 g (0.12 mmol) of palladium (II) acetate in 25 mL of toluene was treated with 0.49 mL (2.9 mmol) of benzophenone imine and heated to 85° C. for 18 h. The crude reaction mixture was diluted with ethyl acetate, filtered through a pad of celite and purified by flash chromatography eluting with a 33% hexanes/ethyl acetate mixture to give 0.65 g (75%) of the title compound as a golden oil.

Workup

customThe crude reaction mixture
filtrationfiltered through a pad of celite
custompurified by flash chromatography
washeluting with a 33% hexanes/ethyl acetate mixture

Sources & evidence

ORD record: ord-73a1e29d9ee54c14b2e7871e28984719
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714009B2

Reaction notes

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