Butylboronic Acid → HCID 68863966, compound

HRID 1725893Notes

Reaction equation

Br[C:2]1[C:3]([CH3:28])=[C:4]([C:15]([NH:18][S:19]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)(=[O:21])=[O:20])=[CH:16][CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:37](B(O)O)[CH2:38][CH2:39][CH3:40]>C1(C)C=CC=CC=1.O>[CH2:37]([C:2]1[C:3]([CH3:28])=[C:4]([C:15]([NH:18][S:19]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)(=[O:20])=[O:21])=[CH:16][CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:6])[CH2:38][CH2:39][CH3:40]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of Example 112A (115 mg, 0.25 mmol), K3PO4 (185 mg, 0.875 mmol), n-butylboronic acid (34 mg, 0.325 mmol), and bis(tricyclohexylphosphine)palladium dichloride (18 mg, 0.025 mmol) in toluene (4 mL) and water (0.2 mL) was purged with nitrogen and stirred at 100° C. for 24 hours. The mixture was then directly chromatographed on a silica gel column, eluting with 30% ethyl acetate/hexanes to provide the desired product (87 mg, 39.7%).

Workup

customThe mixture was then directly chromatographed on a silica gel column
washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-2b60f2654e7f4c83b5695127ff393b71
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491718B2

Reaction notes

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