Potassium Phosphate, Tribasic → HCID 86703773, compound

HRID 1849895Notes

Reaction equation

[CH:1]([N:14]1[CH2:17][CH:16]([O:18][C:19]2[C:31](Cl)=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:21]([F:33])[CH:20]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:34]1(B(O)O)[CH2:36][CH2:35]1.F[B-](F)(F)F.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]([N:14]1[CH2:17][CH:16]([O:18][C:19]2[C:31]([CH:34]3[CH2:36][CH2:35]3)=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:21]([F:33])[CH:20]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl 4-(1-benzhydrylazetidin-3-yloxy)-5-chloro-2-fluorobenzoate (700 mg, 1.50 mmol), cyclopropylboronic acid (258 mg, 3.00 mmol), tricyclohexylphosphine tetrafluoroborate (57 mg, 0.15 mmol), potassium phosphate (954 mg, 4.5 mmol) and palladium acetate (224 mg, 0.15 mmol) in toluene (20 mL) and H2O (1 mL) was stirred at 100° C. for 18 h. The mixture was filtered and diluted with ethyl acetate, washed with brine and concentrated. The residue was purified by silica gel chromatography (eluting with ethyl acetate/ petroleum ether from 0/10 to 1/10) to give target product (650 mg, 92%) as a yellow oil. LCMS (ESI) m/z: 474.2 [M+H].

Workup

filtrationThe mixture was filtered
additiondiluted with ethyl acetate
washwashed with brine
concentrationconcentrated
customThe residue was purified by silica gel chromatography (eluting with ethyl acetate/ petroleum ether from 0/10 to 1/10)

Sources & evidence

ORD record: ord-6e29bd8b8fd44f23b4998605fb04f802
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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