Potassium Carbonate → HCID 71270812, compound

HRID 1525878Notes

Reaction equation

HRID 1525878 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:12]2[CH2:26][CH2:25][C:15]3([O:20][CH2:19][C:18](=[O:21])[N:17]([CH:22]4[CH2:24][CH2:23]4)[CH2:16]3)[CH2:14][CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:44]=[C:43]3[C:38]([CH:39]=[CH:40][CH:41]=[N:42]3)=[CH:37][CH:36]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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].C(Cl)Cl>[CH:22]1([N:17]2[CH2:16][C:15]3([CH2:25][CH2:26][N:12]([CH:8]([C:5]4[CH:6]=[CH:7][C:2]([C:35]5[CH:44]=[C:43]6[C:38]([CH:39]=[CH:40][CH:41]=[N:42]6)=[CH:37][CH:36]=5)=[CH:3][CH:4]=4)[C:9](=[O:11])[CH3:10])[CH2:13][CH2:14]3)[O:20][CH2:19][C:18]2=[O:21])[CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 592961167-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)QuinolineHCID 71270828HCID 71270828, compound

Product 1

HCID 71270812HCID 71270812, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of the crude 9-(1-(4-bromophenyl)-2-oxopropyl)-4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one from Example 24b in 1,4-dioxane (1.5 mL) was treated with 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (0.245 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.0113 mmol), and 2M aq potassium carbonate (0.668 mmol). The reaction vessel was purged with nitrogen and sealed, and the mixture irradiated in a Biotage

Workup

  1. customThe reaction vessel was purged with nitrogen
  2. customsealed
  3. customthe mixture irradiated in a Biotage

Sources & evidence

ORD record
ord-9787c9c11ba94e6f91f538d6234498d9
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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