Potassium Phosphate, Tribasic → HCID 118022350, compound

HRID 575836Notes

Reaction equation

Br[C:2]1[C:10]2[O:9][CH:8]([CH:11]3[CH2:13][CH2:12]3)[CH2:7][C:6]=2[CH:5]=[C:4]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:26][N:27]1[CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]1=[O:46]>O1CCOCC1.O.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]>[CH:11]1([CH:8]2[CH2:7][C:6]3[CH:5]=[C:4]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=[C:2]([C:35]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[C:28](=[O:46])[N:27]([CH3:26])[CH:36]=4)[C:10]=3[O:9]2)[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of the title compound from Step 2 (80 mg, 252 umol) in dioxane (10.00 mL) and H2O (1.00 mL) was added Pd(dppf)Cl2 (9 mg, 12.61 umol), K3PO4 (134 mg, 631 umol) and 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one (79 mg, 278 umol) in one portion. The reaction mixture was degassed with N2 and heated to 90° C. for 3 hours. It was then concentrated and purified by prep-HPLC to give the title compound (18.36 mg, 19% yield). 1H NMR (CDCl3, 400 MHz) δ 8.53-8.51 (d, J=8.0 Hz, 1H), 7.79 (s, 1H), 7.75 (s, 1H), 7.63-7.56 (m, 2H), 7.33-7.31 (d, J=8.0 Hz, 1H), 7.15 (s, 1H), 4.43-4.37 (m, 1H), 3.68 (s, 3H), 3.50-3.46 (m, 1H), 3.32-3.16 (m, 1H), 3.09 (s, 3H), 1.21-1.06 (m, 1H), 0.60-0.59 (m, 2H), 0.39-0.32 (m, 2H). LCMS: 396.0 (M+1)+

Workup

customThe reaction mixture was degassed with N2
concentrationIt was then concentrated
custompurified by prep-HPLC

Sources & evidence

ORD record: ord-add90901e49f4aed89c5786da7cddfd9
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

Loading…