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Triethylamine → 4-(6-Cyano-pyridin-3-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1177161
Notes
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Reaction equation

HRID 1177161 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)O1.[CH3:18][N:19]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[CH:37]=[C:36]([OH:38])[C:30]3[CH2:31][C:32]([CH3:35])([CH3:34])[O:33][C:29]=3[CH:28]=2)=[O:26])=[N:20]1.CCN(CC)CC>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:18][N:19]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[CH:37]=[C:36]([O:38][C:9]3[CH:14]=[N:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=3)[C:30]3[CH2:31][C:32]([CH3:35])([CH3:34])[O:33][C:29]=3[CH:28]=2)=[O:26])=[N:20]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 164141882-Cyanopyridine-5-boronic acid pinacol esterHCID 595600842,3-Dihydro-4-hydroxy-2,2-dimethyl-N-(1-methyl-1H-pyrazol-3-yl)-6-benzofurancarboxamide

Product 1

HCID 667561004-(6-Cyano-pyridin-3-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amideYield 47.5%

Reagents, catalysts & solvents 2

HCID 8895
Cupric acetate
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile (634 mg, 2.76 mmol), 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (31a) (396 mg, 1.33 mmol), Et3N (0.96 mL, 6.89 mmol), and Cu(OAc)2 (501 mg, 2.76 mmol) in CH2Cl2 (15 mL) was stirred at room temperature with 4A molecular sieves for 4 days, then filtered through celite, washed with CHCl3, concentrated, and purified by column chromatography with 30-60% EtOAc in hexanes to give a white foam (246 mg, 46% yield). 1H NMR (400 MHz, CDCl3) δ 9.23 (s, 1 H) 8.45 (d, J=2.53 Hz, 1 H) 7.65 (d, J=8.59 Hz, 1 H) 7.21-7.35 (m, 2 H) 7.10 (d, J=111.37 Hz, 2 H) 6.78 (d, J=2.02 Hz, 1 H) 3.73 (s, 3 H) 2.89 (s, 2 H)) 1.48 (s, 6 H); LCMS for C21H19N5O3 m/z 390.00 (M+H+).

Workup

  1. filtrationfiltered through celite
  2. washwashed with CHCl3
  3. concentrationconcentrated
  4. custompurified by column chromatography with 30-60% EtOAc in hexanes

Sources & evidence

ORD record
ord-e384ff04f4394c26822c36e457305f15
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842713B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes