Potassium Acetate → [4-(Dihydroxyboranyl)-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl]methyl acetate

HRID 592844Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6]1[C:7]([N:13]2[CH2:24][CH2:23][N:22]3[C:15](=[CH:16][C:17]4[CH2:18][C:19]([CH3:26])([CH3:25])[CH2:20][C:21]=43)[C:14]2=[O:27])=[N:8][CH:9]=[CH:10][C:11]=1Cl)(=[O:3])[CH3:2].[B:28]1(B2OC(C)(C)C(C)(C)O2)[O:32]C(C)(C)C(C)(C)[O:29]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])(=O)C.[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[C:1]([O:4][CH2:5][C:6]1[C:7]([N:13]2[CH2:24][CH2:23][N:22]3[C:15](=[CH:16][C:17]4[CH2:18][C:19]([CH3:26])([CH3:25])[CH2:20][C:21]=43)[C:14]2=[O:27])=[N:8][CH:9]=[CH:10][C:11]=1[B:28]([OH:32])[OH:29])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 199d (4.5 g, 1.0 eq., 11.6 mmol), Pin2B2 (7.38 g, 2.5 eq., 29.0 mmol), PdCl2(dppf) (473 mg, 0.05 eq., 0.58 mmol), x-phos (470 mg, 0.1 eq., 1.16 mmol), potassium acetate (3.41 g, 3.0 eq., 34.8 mmol), and dioxane (100 mL). After three cycles of vacuum/argon flush, the mixture was heated at 65° C. for 4 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure to afford crude 199e as a brown-red liquid (4.0 g, purity: 65%). MS-ESI: [M+H]+ 398.3.

Workup

customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
customAfter three cycles of vacuum/argon flush
temperatureIt was then cooled to room temperature
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-5f8e2fce8db847bfa6753b5ff9cbceb7
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238655B2

Reaction notes

Loading…