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Potassium Phosphate, Tribasic → tert-Butyl N-(4-{2-[(1S)-1-{[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]pyridin-4-yl}pyridin-3-yl)carbamate

HRID 1481294
Notes
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Reaction equation

HRID 1481294 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][CH:10]=[CH2:11])[CH:3]=1.[C:20]([O:24][C:25]([NH:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][C:33]=1B(O)O)=[O:26])([CH3:23])([CH3:22])[CH3:21].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1>[C:15]([O:14][C:13]([NH:12][C@H:8]([C:4]1[CH:3]=[C:2]([C:33]2[CH:32]=[CH:31][N:30]=[CH:29][C:28]=2[NH:27][C:25](=[O:26])[O:24][C:20]([CH3:22])([CH3:21])[CH3:23])[CH:7]=[CH:6][N:5]=1)[CH2:9][CH:10]=[CH2:11])=[O:19])([CH3:18])([CH3:17])[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 15366412(3-((tert-Butoxycarbonyl)amino)pyridin-4-yl)boronic acidHCID 66744734Carbamic acid, N-[(1S)-1-(4-chloro-2-pyridinyl)-3-buten-1-yl]-, 1,1-dimethylethyl ester

Product 1

HCID 131736624tert-Butyl N-(4-{2-[(1S)-1-{[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]pyridin-4-yl}pyridin-3-yl)carbamateYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To 1C (1.080 g, 3.82 mmol) and (3-((tert-butoxycarbonyl)amino)pyridin-4-yl)boronic acid (1 g, 4.20 mmol) in a sealable flask was added THF (19.09 ml), potassium phosphate tribasic (5.09 ml, 15.28 mmol) and degassed with Ar. (DtBPF)PdCl2 (0.249 g, 0.382 mmol) was added, degassed further. The reaction mixture was heated at 75° C. for overnight. Then, the mixture was washed with water and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, concentrated and purified by ISCO to yield 72A as brown solid (670 mg, 40%). 1H NMR (500 MHz, METHANOL-d4) δ 8.65 (br. s., 1H), 8.62-8.57 (m, 1H), 8.46 (d, J=5.0 Hz, 1H), 7.46 (s, 1H), 7.41 (d, J=5.2 Hz, 1H), 7.39 (m, 1H), 5.86-5.75 (m, 1H), 5.15-5.03 (m, 2H), 4.81-4.75 (m, 1H), 2.68-2.57 (m, 1H), 2.55-2.46 (m, 1H), 1.46-1.27 (m, 18H).

Workup

  1. customdegassed with Ar
  2. customdegassed further
  3. washThen, the mixture was washed with water
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by ISCO

Sources & evidence

ORD record
ord-64b87fdc8e9b48239d5912f4bd06e57b
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409908B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes