Toluene → HCID 54085371, compound

HRID 1600991Notes

Reaction equation

Br[C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C@H:8]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[C:4]([C:27]([F:30])([F:29])[F:28])[CH:3]=1.[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[Si:18]([O:17][C@H:8]([CH2:9][CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:7][O:6][C:5]1[CH:25]=[CH:26][C:2]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:3][C:4]=1[C:27]([F:30])([F:29])[F:28])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 120 °C

Procedure

Prepared according to the method as described in Example 33a) from (2R)-1-(4-bromo-2-trifluoromethylphenoxy)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)butane (1.0 g, ~67% pure), benzeneboronic acid (0.18 g), tetrakis(triphenylphosphine)palladium(0) (0.035 g), toluene (10 ml), ethanol (2 ml) and aqueous sodium carbonate (2 M, 1.45 ml) with heating at 120° C. for 1 hour. After work up the residue was purified by chromatography over silica eluting with ethyl acetate:hexane (1:9) to give an impure sample of the sub-title compound as a light brown oil (0.80 g, ~67% pure).

Workup

customPrepared
customAfter work up the residue was purified by chromatography over silica eluting with ethyl acetate:hexane (1:9)

Sources & evidence

ORD record: ord-97d8e4cafa354e38b70fca761a82a896
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977105

Reaction notes

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