Potassium Carbonate → HCID 118022585, compound

HRID 518567Notes

Reaction equation

HRID 518567 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([CH2:12][CH3:13])[CH2:8][CH2:7]2.[CH3:19][N:20]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:39].C([O-])([O-])=O.[K+].[K+]>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]>[CH2:12]([CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([C:28]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21](=[O:39])[N:20]([CH3:19])[CH:29]=3)[CH:3]=[C:4]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:5]=2)[O:10]1)[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 118021825HCID 118021825, compoundHCID 1238094992-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1(2H)-one

Product 1

HCID 118022585HCID 118022585, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
85 °C

Procedure

A mixture of the title compound from Step 6 (105 mg, 0.315 mmol), 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one (108 mg, 0.379 mmol), K2CO3 (131 mg, 0.949 mmol) and Pd(dppf)Cl2 (23.1 mg, 0.032 mmol) in dioxane/H2O (10 mL/3 mL) was heated to 85° C. for 2 h. It was then filtered and extracted with EtOAc. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE/EA 50:1 to 20:1 to 10:1) to give the title compound (25 mg, 19%). 1H NMR (400 MHz, CD3OD) δ 8.31 (d, J=8.4 Hz, 1H), 7.59-7.55 (m, 1H), 7.47-7.43 (m, 1H), 7.31-7.23 (m, 2H), 7.05 (s, 1H), 6.95 (d, J=2.8 Hz, 1H), 3.77-3.71 (m, 1H), 3.60 (s, 3H), 2.95-2.75 (m, 5H), 1.95-1.92 (m, 1H), 1.66-1.54 (m, 1H), 1.38-1.22 (m, 2H), 0.59-0.55 (m, 1.25H), 0.42-0.38 (m, 1.75H). LCMS: 413.0 (M+1)+.

Workup

  1. filtrationIt was then filtered
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (PE/EA 50:1 to 20:1 to 10:1)

Sources & evidence

ORD record
ord-2305d39f12c847b0b81136361d1c25a0
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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