Sodium Hydroxide → HCID 178424479, compound

HRID 1014788Notes

Reaction equation

HRID 1014788 reaction equation
I[C:2]1[C-:3]([N:7]([CH3:9])[CH3:8])[CH:4]=[CH:5][CH:6]=1.[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>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.COCCOC>[CH3:16][C:17]1[CH:10]=[C:14]([C:2]2[C-:3]([N:7]([CH3:9])[CH3:8])[CH:4]=[CH:5][CH:6]=2)[CH:13]=[CH:12][CH:11]=1.[CH-:18]1[CH:19]=[CH:20][CH:21]=[CH:16]1.[Fe+2:15]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 66827Phenylboronic AcidHCID 178482625HCID 178482625, compound

Product 1

HCID 178424479HCID 178424479, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Racemic iodide 12i (102 mg, 0.29 mmol), PhB(OH)2 (78 mg, 0.57 mmol) and Pd(PPh3)4 (33 mg, 2.86×10−2 mmol) were added to a dry Schlenk flask, followed by DME (3 mL) and an aqueous solution of 3 M aqueous NaOH (0.25 mL, 0.70 mmol). Argon was bubbled through the resulting mixture for 10 minutes, and the system was heated at reflux for 17 h. The reaction was allowed to cool to room temperature, diluted with Et2O, washed with water (1×5 mL), brine (1×5 mL), dried over Na2SO4, filtered, and all volatiles were removed in vacuo. Flash column chromatography (silica gel, 98:2 hexane/EtOAc) afforded 56 (85 mg, 93%) as an orange oil: Rf 0.41 (90:10 hexane/EtOAc); IR (KBr, CHCl3) vmax 3093, 2940, 2848, 2778, 1605, 1487, 1452, 1416 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.61 (d, 1H, J=7.8 Hz), 7.49 (s, 1H), 7.23 (t, 1H, J=7.5 Hz), 7.04 (d, 1H, J=7.5 Hz), 4.23 (s, 1H), 4.18 (s, 5H), 4.11 (s, 1H), 4.02 (t, 1H, J=2.7 Hz), 2.52 (s, 6H), 2.39 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 139.0, 137.1, 129.0, 127.7, 126.7, 125.7, 112.4, 77.9, 69.1, 66.7, 62.2, 58.1, 44.6, 21.5; EIMS [m/z (%)] 319 (M+, 100); HRMS (EI) calcd for C19H21N56Fe: 319.1023. Found 319.1025.

Workup

  1. customArgon was bubbled through the resulting mixture for 10 minutes
  2. temperaturethe system was heated
  3. temperatureat reflux for 17 h
  4. additiondiluted with Et2O
  5. washwashed with water (1×5 mL), brine (1×5 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customall volatiles were removed in vacuo

Sources & evidence

ORD record
ord-1aafb000b6934aa886b905d64e55f974
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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