Potassium Phosphate, Tribasic → 5-[3,4-Dimethoxy-2-(3-methoxymethyl-oxetan-3-ylmethoxy)-phenyl]-3H-isobenzofuran-1-one

HRID 2171054Notes

Reaction equation

Br[C:2]1[C:7]([O:8][CH2:9][C:10]2([CH2:14][O:15][CH3:16])[CH2:13][O:12][CH2:11]2)=[C:6]([O:17][CH3:18])[C:5]([O:19][CH3:20])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[C:34](=[O:38])[O:33][CH2:32]3)O1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:18][O:17][C:6]1[C:7]([O:8][CH2:9][C:10]2([CH2:14][O:15][CH3:16])[CH2:13][O:12][CH2:11]2)=[C:2]([C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[C:34](=[O:38])[O:33][CH2:32]3)[CH:3]=[CH:4][C:5]=1[O:19][CH3:20]

Participants

Conditions

Temperature: 120 °C

Procedure

3-(6-Bromo-2,3-dimethoxy-phenoxymethyl)-3-methoxymethyl-oxetane (0.02 g, 0.06 mmol) and 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-isobenzofuran-1-one (Compound 309) (0.039 g, 0.14 mmol) were dissolved in 1,4-dioxan (0.6 mL). Argon was purged through the solution. Pd2(dba)3 0.001 g, 0.001 mmol) and PCy3 (0.0008 g, 0.003 mmol) were added followed by addition of K3PO4 (0.043 g, 0.2 mmol) in H2O (0.3 mL). The reaction mixture was heated in a microwave oven at 120° C. for 10 min. The mixture was filtrated, concentrated, redissolved in DMSO and purified by preparative HPLC to afford the title compound.

Workup

customArgon was purged through the solution
filtrationThe mixture was filtrated
concentrationconcentrated
dissolutionredissolved in DMSO
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-dba926f8a132457aabb4d3dc77642056
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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