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Sodium Carbonate → Carbamic acid, (4-(4-formylphenyl)-2-pyridinyl)-, 1,1-dimethylethyl ester

HRID 1245475
Notes
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Reaction equation

HRID 1245475 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.[CH:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:16]([C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=2)=[CH:20][CH:19]=1)=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 11484026(4-Iodo-Pyridin-2-Yl)-Carbamic Acid Tert-Butyl Ester

Product 1

HCID 21912851Carbamic acid, (4-(4-formylphenyl)-2-pyridinyl)-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (90 mg, 0.08 mmol, 0.05 equiv) was added to a deoxygenated mixture of tert-butyl 4-iodopyridin-2-ylcarbamate (1-1, 0.500 g, 1.56 mmol, 1 equiv), 4-formylphenyl boronic acid (351 mg, 2.34 mmol, 1.50 equiv), and aqueous saturated sodium carbonate solution (2.0 M, 2.3 mL, 4.7 mmol, 3.0 equiv) in dioxane (15 mL), and the resulting mixture was heated at reflux for 18 h. The reaction mixture was cooled then concentrated. The residue was partitioned between half-saturated aqueous NaCl solution (100 mL) and EtOAc (100 mL). The organic layer was dried over sodium sulfate, and concentrated to give tert-butyl 4-(4-formylphenyl)pyridin-2-ylcarbamate (2-1) as an off-white solid. LRMS m/z (M+H) Calcd: 242.2 (minus t-Bu), 199.2 (minus Boc); found 243.0 and 199.0.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationthen concentrated
  5. customThe residue was partitioned between half-saturated aqueous NaCl solution (100 mL) and EtOAc (100 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6745573145bb4ac7be1e9bf674f2a298
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07125888B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes