Sodium Carbonate → (1S,2R)-3-Chloro-4'-(1-ethyl-2-hydroxy-4-pyridin-3-ylbutoxy)biphenyl-4-carbonitrile

HRID 380055Notes

Reaction equation

C([Si](C)(C)[O:6][C@H:7]([CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[C@H:8]([CH2:19][CH3:20])[O:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1)(C)(C)C.Br[C:32]1[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[C:34]([Cl:40])[CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.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>[Cl:40][C:34]1[CH:33]=[C:32]([C:13]2[CH:12]=[CH:11][C:10]([O:9][C@@H:8]([CH2:19][CH3:20])[C@H:7]([OH:6])[CH2:21][CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:15][CH:14]=2)[CH:39]=[CH:38][C:35]=1[C:36]#[N:37]

Participants

Conditions

Temperature: 90 °C

Procedure

Prepared according to the method described in Example 12b) from (1S,2R)-4-[2-(tertbutyldimethylsilanyloxy)-1-ethyl-4-pyridin-3-yl-butoxy]benzeneboronic acid (0.18 g, Example 88b)), 4-bromo-2-chlorobenzonitrile (0.18 g), 2M aqueous sodium carbonate (0.48 ml) and tetrakis(triphenylphosphine)palladium (0) (0.012 g) in ethanol (3 ml) with heating at 90 ° C. for 4 hours. The residue was purified by column chromatography eluting with a gradient of 50-1 00% ethyl acetate in isohexane to give the title compound as a solid (0.125 g).

Workup

customPrepared
customThe residue was purified by column chromatography
washeluting with a gradient of 50-1 00% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-eea73aa86aae47049b132fbdbee55c71
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300352B1

Reaction notes

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