Triphenylphosphine → HCID 86683661, compound

HRID 1509294Notes

Reaction equation

HRID 1509294 reaction equation
Br[C:2]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)=[N:12][C:5]2[O:6][CH2:7][C:8](=[O:11])[N:9]([CH3:10])[C:4]=2[CH:3]=1.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34](B(O)O)[CH:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F-].[Cs+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:10][N:9]1[C:8](=[O:11])[CH2:7][O:6][C:5]2[N:12]=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[C:2]([C:34]3[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=3)=[CH:3][C:4]1=2

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 25953Cesium fluorideHCID 27343783-Pyridinylboronic acidHCID 86683662HCID 86683662, compound

Product 1

HCID 86683661HCID 86683661, compoundYield 21.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Tert-butyl (1-(4-(7-bromo-1-methyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (57 mg, 0.117 mmol), pyridin-3-yl boronic acid (21.52 mg, 0.175 momol), triphenylphosphine (9.18 mg, 0.035 mmol), cesium fluoride (89 mg, 0.584 mmol) were dissolved in 1,2-dimethoxyethane (2 ml) to give an orange solution. The reaction mixture was degassed by bubbling nitrogen for 10 minutes. Palladium(II)acetate (3.93 mg, 0.018 mmol) was added at room temperature. The resulting reaction was degassed and heated to 80° C. for 18 hours. The reaction mixture was concentrated to dryness under reduced pressure. The crude was purified by preparatory HPLC to give the title compound (12 mg, 21%). LCMS (Method D) RT 1.158 min, M+1=487. 1H NMR (500 MHz, CDCl3): 7.64-7.52 (1H, m), 7.37-7.21 (8H, m), 4.94 (2H, s), 3.43 (3H, s), 2.59-2.36 (4H, m), 2.15-2.01 (1H, m), 1.91-1.77 (1H, m), 1.47-1.20 (9H, br s).

Workup

  1. customto give an orange solution
  2. customThe reaction mixture was degassed
  3. customby bubbling nitrogen for 10 minutes
  4. customThe resulting reaction
  5. customwas degassed
  6. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  7. customThe crude was purified by preparatory HPLC

Sources & evidence

ORD record
ord-dd86f49b2be6440eb1afbb6df4a68da2
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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