Potassium Phosphate, Tribasic → HCID 86687981, compound

HRID 509374Notes

Reaction equation

HRID 509374 reaction equation
Br[C:2]1[C:3]([C@@H:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH:35](B(O)O)=[CH2:36].CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C>O.CCO.CCOC(C)=O>[F:16][C:15]([F:18])([F:17])[C:12]1[CH:13]=[CH:14][C:9]([C@H:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:3]2[C:2]([CH:35]=[CH2:36])=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 4683185Vinylboronic acidHCID 11714598(4-(N,N-Dimethylamino)phenyl)di-tert-butyl phosphineHCID 71164782(S)-tert-butyl((3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate

Product 1

HCID 86687981HCID 86687981, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of (S)-tert-butyl ((3-bromopyridin-2-yl)(4-(trifluoromethyl)-phenyl)methyl)carbamate (0.4 g, 0.93 mmol) in water (2 mL) and EtOH (8 mL) were added K3PO4 (0.3 g, 1.3 mmol), vinyl boronic acid (4 mL, 9.3 mmol) and A−taPhos)2PdCl2 (Guram, A. S. et al. Org. Lett. 2006, 8, 1787; 0.13 g, 0.01 mmol). The resulting mixture was stirred at 120° C. for 1 h. Reaction progress was monitored by TLC (20% EtOAc in petroleum ether). After completion of reaction, water (50 mL) was added to the reaction mixture, and the product was extracted with DCM (3×25 mL). The combined organic layers were separated, dried over anhydrous sodium sulfate, and purified by column chromatography using silica (100-200 mesh) and using 15-30% EtOAc in petroleum ether as an eluent. In this manner, (S)-tert-butyl ((4-(trifluoromethyl)phenyl)(3-vinylpyridin-2-yl)methyl)carbamate was obtained as an off-white solid. MS (ESI pos. ion) m/z: 378.9 (M+1).

Workup

  1. customReaction progress
  2. additionwas added to the reaction mixture
  3. extractionthe product was extracted with DCM (3×25 mL)
  4. customThe combined organic layers were separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-a0fb20d6c345436db1e95824f6aadeea
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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