Sodium Hydroxide → HCID 178482622, compound

HRID 1014787Notes

Reaction equation

HRID 1014787 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.C(COC)OC>[C:16]1([C:2]2[C-:3]([N:7]([CH3:9])[CH3:8])[CH:4]=[CH:5][CH:6]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15]

Participants

6

Reactant 3

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

Product 1

HCID 178482622HCID 178482622, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
55 °C

Procedure

Racemic iodide 12i (89 mg, 0.25 mmol), PhB(OH)2 (34 mg, 0.28 mmol) and Pd(PPh3)4 (29 mg, 2.51×10−2 mmol) were added to a dry Schlenk flask, followed by dimethoxyethane (DME, 2 mL) and an aqueous solution of 3 M NaOH (0.17 mL, 0.50 mmol). Argon was bubbled through the resulting mixture for 10 minutes, and the system was heated at 55° C. for 14 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 55 (61 mg, 80%) as an orange oil: Rf 0.45 (90:10 hex/EtOAc); IR (KBr, CHCl3) vmax 3091, 2941, 2852, 2779, 1601, 1491, 1444, 1416 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.80-7.74 (m, 2H), 7.36-7.19 (m, 3H), 4.28-4.25 (m, 1H), 4.18 (s, 5H), 4.15-4.11 (m, 1H), 4.05 (t, 1H, J=2.7 Hz), 2.53 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 139.1, 128.4, 127.8, 125.9, 112.5, 78.1, 69.2, 66.5, 62.4, 58.0, 44.6; EIMS [m/z (%)] 305 (M+, 100); HRMS (EI) calcd for C18H19N56Fe: 305.0867. Found 305.0864.

Workup

  1. customArgon was bubbled through the resulting mixture for 10 minutes
  2. temperatureto cool to room temperature
  3. additiondiluted with Et2O
  4. washwashed with water (1×5 mL), brine (1×5 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customall volatiles were removed in vacuo

Sources & evidence

ORD record
ord-4e8b365afb6b427992dbd55afc0d4283
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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