Potassium Phosphate, Tribasic → HCID 71767099, compound

HRID 516973Notes

Reaction equation

HRID 516973 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]([NH:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:32][CH:31]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:40]1[CH2:41][CH2:42][N:37]([CH2:36][C:33]2[CH:32]=[CH:31][C:30]([C:2]3[CH:11]=[C:10]([C:12]([NH:14][CH2:15][CH2:16][N:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)=[O:13])[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=3)=[CH:35][CH:34]=2)[CH2:38][CH2:39]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27955024-((Morpholino)methyl)phenylboronic acid pinacol esterHCID 606827052-chloro-N-(2-pyrrolidin-1-ylethyl)quinoline-4-carboxamide

Product 1

HCID 71767099HCID 71767099, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
130 °C

Procedure

In a sealed 5 ml microwave tubed, a suspension of 2-chloro-N-(2-pyrrolidin-1-ylethyl)quinoline-4-carboxamide (preparation 11) (200 mg, 0.66 mmol), 4-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]morpholine (preparation 2) (399 mg, 1.31 mmol), potassium phosphate (419 mg, 1.97 mmol) and tetrakis(triphenylphosphine)palladium (0) (22 mg, 0.02 mmol) in DMF/Water 3/1 (4 ml) was heated at 130° C. under microwave irradiation for 30 minutes. The reaction was filtered through Celite™ and solvents were removed under reduced pressure. The resulting residue was taken up in DCM (50 ml) and washed with NaHCO3 saturated aqueous solution (25 ml). The organic layer was separated and dried over MgSO4 before concentration to dryness. The reaction crude was purified by preparative HPLC. The fractions containing product were pooled together and freeze dried to obtain the desired compound as a white solid (220 mg, 0.49 mmol, Yield 57%).

Workup

  1. filtrationThe reaction was filtered through Celite™ and solvents
  2. customwere removed under reduced pressure
  3. washwashed with NaHCO3 saturated aqueous solution (25 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4 before concentration to dryness
  6. customThe reaction crude
  7. customwas purified by preparative HPLC
  8. additionThe fractions containing product
  9. customfreeze dried

Sources & evidence

ORD record
ord-87fc248d19d045c5ab9a7f2a19f1c7aa
Source dataset
uspto-grants-2015_08
Patent number
US09115088B2

Reaction notes

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