Potassium Carbonate → HCID 71270799, compound

HRID 1525875Notes

Reaction equation

HRID 1525875 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:14]2[CH2:28][CH2:27][C:17]3([O:22][CH2:21][C:20](=[O:23])[N:19]([CH:24]4[CH2:26][CH2:25]4)[CH2:18]3)[CH2:16][CH2:15]2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:4]([F:29])[CH:3]=1.CC1(C)C(C)(C)OB([C:38]2[CH:47]=[C:46]3[C:41]([CH:42]=[CH:43][CH:44]=[N:45]3)=[CH:40][CH:39]=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:24]1([N:19]2[CH2:18][C:17]3([CH2:27][CH2:28][N:14]([CH:8]([C:5]4[CH:6]=[CH:7][C:2]([C:38]5[CH:47]=[C:46]6[C:41]([CH:42]=[CH:43][CH:44]=[N:45]6)=[CH:40][CH:39]=5)=[CH:3][C:4]=4[F:29])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:15][CH2:16]3)[O:22][CH2:21][C:20]2=[O:23])[CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 592961167-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)QuinolineHCID 71270813HCID 71270813, compound

Product 1

HCID 71270799HCID 71270799, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 3-(4-bromo-2-fluorophenyl)-3-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)propanoate (1.924 mmol) in 1,4-dioxane (6 mL) was treated with 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (2.116 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.096 mmol) and 2M aq potassium carbonate (5.77 mmol). The reaction vessel was purged with nitrogen and sealed, and the mixture was irradiated in a Biotage Initiator Microwave at 120° C. for 15 min. The resulting black mixture was diluted with water (50 mL) and extracted with dichloromethane three times. The combined organic layer was treated with Silicycle Si-thiol (100 mg), dried over sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by silica gel chromatography (0-7% methanol/dichloromethane) afforded the title compound as a brown solid (802 mg, 72% yield). MS(ES)+ m/e 518.4 [M+H]+.

Workup

  1. customThe reaction vessel was purged with nitrogen
  2. customsealed
  3. customthe mixture was irradiated in a Biotage Initiator Microwave at 120° C. for 15 min
  4. additionThe resulting black mixture was diluted with water (50 mL)
  5. extractionextracted with dichloromethane three times
  6. additionThe combined organic layer was treated with Silicycle Si-thiol (100 mg)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification of the residue by silica gel chromatography (0-7% methanol/dichloromethane)

Sources & evidence

ORD record
ord-295bc10a50934462b12a239def413b5e
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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