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Nitrogen → tert-butyl (S)-(1-(4-methyl-2'-(trifluoromethyl)-[3,4'-bipyridin]-6-yl)ethyl)carbamate

HRID 57501
Notes
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Reaction equation

HRID 57501 reaction equation
N#N.[C:3]([O:7][C:8](=[O:20])[NH:9][C@H:10]([C:12]1[CH:17]=[C:16]([CH3:18])[C:15](Br)=[CH:14][N:13]=1)[CH3:11])([CH3:6])([CH3:5])[CH3:4].[F:21][C:22]([F:33])([F:32])[C:23]1[CH:28]=[C:27](B(O)O)[CH:26]=[CH:25][N:24]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CCOC(C)=O>[C:3]([O:7][C:8](=[O:20])[NH:9][C@H:10]([C:12]1[N:13]=[CH:14][C:15]([C:27]2[CH:26]=[CH:25][N:24]=[C:23]([C:22]([F:33])([F:32])[F:21])[CH:28]=2)=[C:16]([CH3:18])[CH:17]=1)[CH3:11])([CH3:6])([CH3:5])[CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 451588802-(Trifluoromethyl)pyridine-4-boronic acidHCID 90451674(S)-tert-butyl (1-(5-bromo-4-methylpyridin-2-yl)ethyl)carbamate

Product 1

HCID 90451687tert-butyl (S)-(1-(4-methyl-2'-(trifluoromethyl)-[3,4'-bipyridin]-6-yl)ethyl)carbamateYield 82.6%

Reagents, catalysts & solvents

2
HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

N2 was bubbled through a solution of (S)-tert-butyl(1-(5-bromo-4-methylpyridin-2-yl)ethyl)carbamate (200 mg, 0.635 mmol), (2-(trifluoromethyl)pyridin-4-yl)boronic acid (145 mg, 0.761 mmol) and Na2CO3 (2.0 M, 635 μl, 1.269 mmol) in dioxane for 5 min. Cl2Pd(dppf) (CH2Cl2 adduct) (51.8 mg, 0.063 mmol) was added. The reaction mixture was stirred at 90° C. for 16 hr. The mixture was diluted with EtOAc, washed with water, brine, dried over Na2SO4, filtered, concentrated and purified through flash column chromatography (0-100% EtOAc/Heptane) to give 200 mg (S)-tert-butyl(1-(4-methyl-2′-(trifluoromethyl)-[3,4′-bipyridin]-6-yl)ethyl)carbamate as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.83 (d, J=4.9 Hz, 1H), 8.36 (s, 1H), 7.66 (s, 1H), 7.51-7.42 (m, 1H), 7.21 (s, 1H), 5.60 (d, J=7.7 Hz, 1H), 4.87 (p, J=6.9 Hz, 1H), 2.30 (s, 3H), 1.48 (d, J=6.9 Hz, 3H), 1.45 (s, 9H). MS m/z 382.3 (M+H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified through flash column chromatography (0-100% EtOAc/Heptane)

Sources & evidence

ORD record
ord-98e2c8b0f4f348fd901f5a2a1e05f29b
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434719B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes