Acetonitrile → HCID 68667474, compound

HRID 1423362Notes

Reaction equation

OB(O)[C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([OH:10])=[O:9].[Br:12][C:13]1[CH:18]=[CH:17][C:16](I)=[CH:15][C:14]=1[O:20][CH3:21].CC#N.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:3]2[CH:7]=[CH:6][S:5][C:4]=2[C:8]([OH:10])=[O:9])=[CH:15][C:14]=1[O:20][CH3:21]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 3-(dihydroxyboryl)thiophene-2-carboxylic acid (1.89 g, 10.85 mmol) and 1-bromo-4-iodo-2-methoxybenzene (3.09 g, 9.86 mmol) in a 3:1 mixture of MeCN:H2O (100 mL) was treated with K2CO3 (4.09 g, 29.6). Pd(OAc)2 (66.4 mg, 0.30 mmol) and biphenyl-2-yl(dicyclohexyl)phosphine (207 mg, 0.59 mmol) were added and the mixture was stirred at 90° C. for 3 h. The mixture was cooled and concentrated, and the residue was added at 0° C. to a mixture of 10% aqueous NaOH (100 mL) and DCM. The mixture was acidified to pH=1 by addition of aqueous HCl (6 N) and the solid precipitate was collected by filtration, washed with cold H2O and DCM, then dried to afford the title compound (2.29 g, 74%). LCMS (ES+) m/z 313, 315 (M+H)+.

Workup

temperatureThe mixture was cooled
concentrationconcentrated
additionthe residue was added at 0° C. to a mixture of 10% aqueous NaOH (100 mL) and DCM
additionThe mixture was acidified to pH=1 by addition of aqueous HCl (6 N)
filtrationthe solid precipitate was collected by filtration
washwashed with cold H2O and DCM
customdried

Sources & evidence

ORD record: ord-5e52ad3562e148e99d400a0442d07956
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927569B2

Reaction notes

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