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Water → Methyl 4-amino-3-chloro-6-(7-fluoro-2-phenyl-1,3-benzoxazol-6-yl)pyridine-2-carboxylate

HRID 708932
Notes
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Reaction equation

HRID 708932 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Br)[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[Cl:13].[F:14][C:15]1[C:23]2[O:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:20][C:19]=2[CH:18]=[CH:17][C:16]=1B(O)O.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[C:6]([C:16]2[CH:17]=[CH:18][C:19]3[N:20]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:22][C:23]=3[C:15]=2[F:14])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[Cl:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 22677536Methyl 4-amino-6-bromo-3-chloropicolinateHCID 71240109(7-Fluoro-2-phenyl-1,3-benzoxazol-6-yl)boronic acid

Product 1

HCID 71239870Methyl 4-amino-3-chloro-6-(7-fluoro-2-phenyl-1,3-benzoxazol-6-yl)pyridine-2-carboxylateYield 36%

Reagents, catalysts & solvents

2
HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

0.024 g (0.03 mmol) of (PPh3)2PdCl2 is added to a solution of 0.3 g (1.13 mmol) of methyl 4-amino-6-bromo-3-chloropyridine-2-carboxylate in 20 ml of dioxane, and this mixture is stirred at room temperature (RT) for 30 min. In succession, 0.35 g (1.35 mmol) of (7-fluoro-2-phenyl-1,3-benzoxazol-6-yl)boronic acid, 0.47 g (3.4 mmol) of K2CO3 and 2 g (111 mmol) of H2O are then added to this mixture, which is then stirred under reflux for 6 h. The mixture is allowed to stand at RT for a further 12 h and then added to 40 ml of H2O. This mixture is extracted repeatedly with CH2Cl2, and the combined organic phase is dried over Na2SO4 and then concentrated. Purification by chromatography on silica gel using the mobile phase heptane/ethyl acetate (3/7) gives 0.16 g (36%) of product. 1H-NMR (CDCl3): δ 8.30, 8.00, 7.55 (3m, 5H, C6H5), 7.60, 7.55 (2d, 2H, benzoxazole ring), 7.30 (s, 1H, pyridine) 4.85 (bs, 2H, NH2), 4.00 (S, 3H, COOCH3).

Workup

  1. stirringis then stirred
  2. temperatureunder reflux for 6 h
  3. waitto stand at RT for a further 12 h
  4. extractionThis mixture is extracted repeatedly with CH2Cl2
  5. dry with materialthe combined organic phase is dried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by chromatography on silica gel using the mobile phase heptane/ethyl acetate (3/7)

Sources & evidence

ORD record
ord-23dc1d51197d454ebbd2f67c0bd273fd
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09179676B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes